Archive of Our Own ^beta

You pulled your coat tighter around yourself as you walked down the sidewalk. You smiled at the decorations as you passed. You loved the holidays. Your went to get yourself a ‘fancy’ coffee, standing in line. It was t too busy just yet, thankfully. You ordered and looked around as you waited. You caught someone’s eye and instantly blushed. You weren’t used to that. Looking away, you assumed it was a fluke. You rushed up to get your drink when your name was cashed. “Thank you.” 

They smiled and nodded. “For Dean?” They called out. You tried to move out of the way, but bumped into him. 

“Sorry.” He gave you a small smile. 

“It’s okay.” You assured him. He was the one that smiled at you a moment ago. “Enjoy your drink.” You said softly before making your way towards the door. You sipped your drink once you were outside, smiling at the flavor. It was winter in a cup. 

“Excuse me?” Someone tapped your shoulder.

Turning, you looked a bit confused. “Yes?”

“Just wanted to asked where you got that beanie? My brother loves those books.” The man from the shop asked. “It'll be a damn good Christmas present.”

You blushed. “There’s a store on the next block. Has a ton of things.” You told him. “They’re having a sale.”

He beamed. “Thanks.” He winked. “I owe you.” He enjoyed how you blushed. “I’m Dean.” He mentioned. 

“Y/N. Nice to meet you.” You said shyly.  

He grinned wider. “What kind of coffee did you get?” He asked casually, not wanting the conversation to end. 

“Chestnut praline latte. You?” You were sure he got something simpler. 

He looked at his label. “Sugar cookie.” He grinned. “It’s not too bad. Not my usual black coffee, but not bad.” 

“Did you get it by accident?” You cracked a smile. “Because sugar cookie is so opposite of black coffee.”

“Lost a bet with my brother.” He chuckled. “I assume you like the fancy one you got?” He asked. 

You nodded. “It’s one of my favorites. Winter in a cup.”

He grinned. “That’s a nice way of putting it.” He chuckled. “Well, I don’t want to hold you up from your errands.” He told you. “Enjoy the rest of your day.” 

You smiled. “Thank you. I hope you do, too.” You gave him a small wave. 

“Just. My. Luck.” You sighed. You were enjoying some scenic driving the next day when your car just…stopped. There was no cell service, either. Making sure you were bundled up, you got out of your car, and started walking. You were just glad you had boots on. You were just at the end of the block when you heard a car stop by you. You stiffened slightly, worried. 

“Are you okay?” Came a voice that sounded slightly familiar, making you turn.

“Y/N!” Dean grinned and rushed out of the car. “Why’re you walking when it’s cold as hell?” 

You were surprised to see Dean. “My car broke down. So, I’m headed into town to get my dad to come tow it for me.” 

He looked back to the end of the block. “How about you stay warm in my car while I take a look at it?” He offered. “I’m good with cars. I’ve rebuilt her a couple times from the ground up.” He patted his car.  

You chewed on your lip. You supposed it was better than walking in the cold. “Alright. If you’re sure. I can pay you?” You offered, not wanting him to do this for free. “Please?”

“Depends on what’s wrong, deal?” He smiled. “I don’t want you freezing.” He opened the door for you. “And then I can drive you to your dad’s.” 

“Deal.” You rushed into the warmth and smiled. He got in a moment later, turning around to get you back to your car. “Our town isn’t that big, are you new?” 

He nodded. “Drove through a couple times, but I just got me a place here.” He explained. 

“Random place to pick.” You noted. “No one moves here. People move out.” 

He stayed quiet. “So, you’ve been here your whole life?” He asked as he parked. 

You nodded. “For as long as I can remember.” You shrugged. “Dad moved us here when I was a baby.” 

“Long time.” He put his gloves on before going to check your car out. 

You watched him, wondering what could be wrong with your car. You hoped nothing expensive. You chewed on your lip as he came back to you.

“Think your battery just died. Easy fix.” He smiled as he got in. “It's probably best to replace it if it’s been a while.” He explained before pulling away. “We can grab the battery and I can replace it.”

“Are they expensive?” You played with your scarf. 

“Not really. On the cheaper side of car repairs. Have you never bought a car battery?” He asked with a chuckle. 

You shook your head. “I don’t know anything about cars, so my dad does all that for me.” You explained. 

“No worries, not a budget breaker.” He assured. “So, what do you do in town?” 

You chuckled nervously. “I sort of own a store. I manage it until it’s officially mine.” You said like it was nothing. 

“Really?” He glanced at you. “That’s cool. What store?” 

You blushed. “Well, it’s a mix of comic books and things for fans. It was that store I mentioned when you asked about my beanie.” You admitted. “I just didn’t want to say ‘hey, I got this at my store’.” 

“You coulda!” He chuckled. “That’s a major thing.” He thought it was cool you were clearly doing something you liked. He drove to the local auto store. “Want to just wait here?” 

“No, because I need to pay.” You chuckled, getting out of the car. “Can I get you lunch as a thanks?” 

“Won’t argue against lunch.” He grinned. “We can go to your favorite place in town? I gotta get to know the best places eventually.”

“Deal.” You smiled. “Thanks.” You got out with him and went inside. “Hi, Kevin.” You smiled at the worker.

“Heya, Y/N.” He waved. “What can we help you with?” He smiled. 

“New car battery.” You shrugged. “Dean can find which one, he’s the car person.” 

Dean waved and held out his hand. “I’m new to town.” He explained. “Nice to meet you.” 

Kevin shook his hand. “It’s rare we get new people in town.” He noted. “Unless you’re moving back, and that’s rarer.” He chuckled. “I think the last person who did that was Y/N’s dad.” 

“Nope, just new.” Dean brushed it off with a grin and went to look at the batteries. While he did that, he could hear you and Kevin chatting and laughing. Once he found the right battery, he went back up front. 

Kevin rang you up and smiled. “See you around. Probably for game night.” He chuckled. 

“Game night?” He asked as you paid.  

You nodded. “We do a game night once a month.” You explained. “Kevin’s the dungeon master when we play D&D, but we play other things, too. Sometimes our whole party can’t make it.” You smiled. 

Kevin nodded. “Sometimes we do board games. Monopoly can get rough.” He noted. “We usually have pizzas and snacks.” 

“How does one get an invitation to this shindig?” Dean grinned. 

“You show up.” You chuckled. “I’ll give you the information.” 

“Sweet. Had a friend who used to play D&D. Though I’m no expert.” Dean nodded. “It’s been awhile.” 

You were surprised he knew what it was, then you felt a bit bad for judging. You thanked Kevin as Dean took the battery out to the car. “See you in a few days.” You told him. 

“See ya.” Kevin waved. “Nice to meet you, Dean.” 

“Likewise, kid.” Dean smiled from outside the door as he held it open for you. “Let’s get your car working again.” He drove you back to your car and it didn’t take long for him to replace it. Soon, your car was on and warming up. 

“Thank you so much.” You were so grateful. “Follow me to lunch?”

“Sounds great.” He winked and went back to his car. 

You blushed and got into your car, pulling away towards town. You doubted he meant anything by his winking and flirting. He seemed like an overall nice guy. You parked at the local diner, hoping he was okay with it. 

He parked next to you and slid out of his car. “Now I can tell this place has killer burgers.” He inhaled the air. “Love these type of places. Do they have milkshakes?” He sounded excited. 

You giggled. “The best milkshakes.” You said as you led him inside, motioning to a booth to sit at. 

He slid in across from you, feeling eyes on him. He’d have to get used to that. One day, he wouldn’t be the new guy. Soon the waitress came over. “Hi, Y/N. Who’s your cute friend?” She asked. 

Blushing, you smiled at her. “Hi, Jess. This is Dean. He’s knew in town. He fixed my car, so I’m repaying him with lunch.”

Jess grinned at Dean. “Welcome to town. Don’t get a lot of new faces.” She offered a menu. “What can I get you to drink?” She asked. 

“I heard you have the best milkshakes.” He grinned. “So, whatever flavor you’d suggest, sweetheart.” 

She chuckled, blushing just slightly. She glanced at you. “Your usual?” She smiled. 

“Please.” You nodded. “Thanks, and add one on for Bobby in the back?”  

“Of course.” She beamed. 

Dean looked at the menu. “I’ll have the burger special.” He handed the menu back to her. 

She took it. “Won’t be long.” She promised and went to put it in. She couldn’t help but glance back to your booth as she put the order in. 

Dean was glancing around and winked at her as she did. “This place is cozy. Bet they have great pancakes?” He asked, eyes going back to you. 

You knew you’d been right. His winking and flirting with you meant nothing. “They do, and even better waffles.” 

“Can’t wait to try it.” He grinned. “When do you go back to the store? I’d like to visit. Get that beanie for Sam.” He noted. “He’s coming to visit the week before Christmas. Maybe I’ll bring him to a game night.” 

“The more, the merrier.” You nodded. You nodded your thanks at Jess as she set your drinks down. 

“Bobby said you spoil him.” She chuckled.

“He deserves it.” You smiled. “He works hard.”  

She grinned. “Your burgers are on the grill.” She assured. 

Dean sipped his milkshake happily as the two of you talked. You seemed so nice! Once she left, he sat back. “You two seem close.” 

“She’s my cousin.” You chuckled.

“Oh.” He grinned. “That works.” 

You wondered if you should mention that she was currently single, but felt that may be a bit weird. “Most people don’t guess that we’re related.” You noted. 

“Small town, makes sense.” He shrugged. 

“What does your brother do?” You smiled after a moment. You were curious if he was into cars like Dean. 

“Finishing up his law degree.” He shrugged. “So proud of him.” He mentioned before sipping his drink. “I think you’d like him. He’s around your guys’ age.” He motioned to you and Jess. “And clearly he’s into the same kinda stuff as you.” 

You didn’t really notice he was older. “Oh, yeah I’m sure he’d fit right in. Does he live far?” You were curious. “If he’s visiting, he can’t be too far, right?” 

“Few hours.” Dean nodded. “I wanted to be closer to him. Our home town is like two days away.” He said as Jess brought your food over. He instantly grinned. “Looks delicious.” He couldn’t wait to dig in. 

Jess beamed. “Hope you like it.” She told him before leaving the two of you to eat.

You ate happily and looked outside at the light snow falling. You loved this time of year.

Dean watched you. “Does the town do holiday stuff?” He wondered. “Like parties or anything?”

You smiled. “Yeah, the school’s do a parade the first day of Christmas break.” You looked back at him. “And there’s the tree lighting on Christmas Eve. Everyone comes out and the shops have little stands.” You explained. 

“Bet that’s fun.” He beamed. “Can’t wait to participate.” He admitted, surprising you slightly. “What?”

“You don’t seem like that festive type.” You admitted. “It took me by surprise that you’re looking forward to that.” 

He shrugged. “I get that a lot.” He assured, finishing his fries. It didn’t seem to bother him all that much, thankfully. 

“Did you want dessert?” You smiled. “They have a really good apple pie.”

“Uh, yeah . Love pie.” He said happily. “It’s the best dessert.” 

You giggled. “It’s in my top five. Maybe.” You told him. “Cupcakes are up there, too.”

“Eh. Agree to disagree.” He teased. “Pecan pie is the best.”

You made a ‘so so’ motion with your hand, giggling at his expression. He gave you a playful shocked look. 

“What’s your favorite, then?” He asked once Jess brought some pie over. 

“I like a good cake, but for pie I’d say berry.” She chuckled. 

“Berry.” He nodded. “That works.” He agreed. “Gotta have that whipped cream on berry, though.” He smirked.

You laughed softly at that. “Yeah.” You sipped your milkshake. You were having a great time. You just had to tell yourself not to have too good of a time, and not to end up getting a crush on him. He was so nice and attractive. It wouldn’t end well for you if you liked him too much. You’d been there. 

At the end of lunch, you went your separate ways with the promise of Dean visiting your store the day of game night.

You were doing some inventory an hour before game night was supposed to start when the doorbell let you know someone came in. “I’ll be right with you.” You told them, not wanting to lose your spot. 

“No worries.” A voice you didn’t recognize said. 

After another minute, you finished that area and went to find the customer. “Anything I can help you find?” 

He smiled at you. “I’m going to a party tonight and want to bring something fun. Maybe one of those themed board games?” 

“Harry Potter or Star Wars?” You smiled. “We also have a few game based ones if that’s what you’re looking for.” You showed him the area. 

The doorbell rang again and you looked over to see Dean. “Dammit Sammy, I told you to wait for me.” He sighed, then saw you and smiled. “Hi, sweetheart.” 

“Oh! This is your brother?!” You grinned. “I’ve heard a lot about you. I’m Y/N. Dean saved my car the second time I met him.” You chuckled. 

“That doesn’t surprise me.” Sam grinned. “I’m Sam. Not Sammy.” He offered his hand to you.

You shook it and grinned up at him before he went back to looking. 

“Hope you don’t mind that I bring him to game night?” Dean asked. 

“I did say the more the merrier.” You teased. “You’re about an hour early, though. I’m just doing some inventory right now.” 

“Can we bring anything else to the party?” Sam asked, holding the game he chose. 

You thought for a minute. “I think everythings covered, but maybe some extra snacks and drinks?” You suggested.  

“We can do that.” Dean grinned. Maybe he’d get a pie to go. “Do you need any help setting up?” 

You shook your head. “No, but thank you.” You smiled. “You’re free to come once I’m done.” You told him. “Kevin usually gets here a few minutes early.” 

“Sweet. We’ll be back.” He handed you the amount for the game. He led Sam out by his arm after seeing how he looked at you. 

“She’s nice.” Sam grinned. “Mom would love her.”

“Yeah, she would.” Dean agreed. “She’s really nice.” He glanced over his shoulder at you through the window. “She was my friend first though, got it?” He looked at Sam. “And you don’t live here. You live hours away.

Sam blinked. “And? They have these things called phones.” He raised an eyebrow at Dean. 

Dean sent him a look and drove them to a store for drinks. He wasn’t sure if you meant alcoholic, so simply got some soda. He debated stopping to get you a coffee.  You seemed to really like it. Maybe he’d get you a fancy steamer. 

“Dean, the gaming store is a block over.” Sam remind him. 

“I’m getting her a coffee. Chill out.” He sent him another look. 

“Oh well excuse me.” He held up his hands as Dean parked in front of the Starbucks.  “Get me one?” He asked. 

“If you tell me what you want? Or just come in?” 

“That praline one.” Sam nodded. 

“The chesnut one?” 

“Yeah!” Sam grinned. “It’s really good. How’d you know about it?”

“That’s what Y/N had when I met her.” Dean explained. “She said it was winter in a cup. So, that’s what I was gonna get her tonight.” 

“Wow, good taste.” Sam liked you already. He couldn’t wait to get back to get to know you more.  

You giggled at something Kevin said as Sam set up the board game he brought. You’d been surprised when Dean handed you your latte, and Kevin was teasing you about it. Kevin told you Dean already knew you too well. “Just because it’s what I was drinking when we met.” You told him quietly. 

“Even better.” Kevin grinned. “He remembered that moment.” He nudged you. 

“I think he may like Jess, so it doesn’t matter.” You nudged him back. 

Jess walked in, as if hearing her name. “I brought left over pastries.” She grinned. “There’s some apple, some cherry, and I think a boston creme.”  She set them down. “What are we playing?” She undid her coat. 

“Oh, pastries!” Kevin went to get one. 

Sam chuckled and waved at Jess. “Hi, I’m Sam. Dean’s brother. I’m visiting for my break.” He introduced himself. 

“I’m Jess. I’m Y/N’s cousin. But we’re almost like sisters.” She grinned, sitting down. 

Dean smirked at them. He could tell when his brother thought someone was attractive. He reached over to get a pastry. “How’s your latte, sweetheart?” He asked you.

You blushed. “Really good.” You nodded. “Thanks, again.” You sipped it. “You didn’t have to.” 

“Wanted to.” He assured. He tossed a napkin at Sam. “Are you gonna explain the game, or continue flirting?” He teased his brother with a smirk.

“Like you aren’t doing the same.” Sam countered.

Jess giggled and smiled at you. “Let’s get this game started.” 

You worked on closing up once game night was over and you had said bye to everyone. You had a lot of fun, and looked forward to the next one. 

“Hey, sweetheart.” Dean came over. “Need a ride home?” He asked, leaning on the counter. 

“That would mean leaving my car here.” You chuckled. You could hear Sam snort from where he was talking to Jess. “But I appreciate the offer.” 

Dean nodded. “Was wondering if you wanted to go to the craft fair together?” He had seen a flyer for it at your shop. “Maybe I can pick you up and we can get coffee first?” 

“I’m actually helping with the fair…” You said shyly. 

“You’re losing your game, Dean!” Sam chuckled, making Jess giggle. 

Your cheeks turned a bright red. “I have a stall there with Kevin.” 

Dean chuckled. “Yeah, I figured you might. Well, thanks for the fun game night.” He smiled. “Have a good night.” He went back to his car, hands in his coat. At least he’d tried to ask you out. You had a way busier life than he did. How could he get a date when you were always doing something? Maybe he’d missed his chance. The thought made him sag.

Sam got in after saying night to Jess. “Hey, I was just messing around.” He saw Dean’s face. 

“What?”

“I don’t think you’re losing your game. Did she say no?” He motioned. 

“Well, yeah. She’s working the fair…thing.” Dean sighed. “And she’s doing Christmas Eve. She might be too busy for dating.” He said sadly. 

“Maybe. Being a store owner is a lot of work.” Sam nodded. “But maybe see if you can bring her dinner at work?” 

“Maybe.” He agreed. “You and Jess? How’s that?” He wondered. 

“Great.” He shrugged. “Not doing much since I live far.” He pointed out, as Dean had already reminded him. “But I did get her number.” 

“Sweet. Least one of us did.” Dean drove them to his place. 

“You don’t have Y/N’s number? Want me to ask Jess for it for you?” He offered. 

Dean thought about it. “Nah, better get it from her. Thanks though.” He said truthfully. “Don’t want her to be weirded out.” 

Sam nodded. “Good luck, man. She’s nice.” He smiled. He hoped the best for his brother. 

Dean walked through the craft fair, trying to give each vendor some business. Even if he didn’t ‘need’ whatever he bought. His mom could use it, right? He waved when he saw you and Kevin. He smiled a bit wider, as well. “Hey, Y/N. Hey Kevin.” 

“Oh. Perfect timing.” Kevin just walked away. 

You blushed brightly. “Hi, Dean.” You greeted him. “Enjoying the craft fair.”

“Yeah, everyone’s so nice.” He nodded. “Got some stuff for my mom.”

You smiled. “Good.” You said happily. 

He looked at your stuff. “Did you make this stuff?” 

You nodded. “Yeah. One of the requirements.” You told him. 

“I’ll get one.” He got a calendar. 

You smiled at that. “Awesome. That’ll be $15. Do you want a bag?” 

“Wait.” He also got a key chain. “There. Yes, please.” He nodded. “Thank you.” He took the bag as you handed it to him. “Are you free anytime this week?” He asked, hopeful. 

You thought. “I have Wednesday evening free.” 

“Would you like to do something together?” He smiled. “Dinner? Movie?” He suggested. 

“Don’t bother, man. She won’t put out.” A voice said to Dean in passing, making you sigh.

Dean frowned at the guy instantly. “And who the hell are you?” 

“No one.” You said quickly. “Doesn’t matter.” You told him. “Pick me up at the shop at 5?” You asked Dean. 

Dean glared at the guy, daring him to say something. “Yeah, sweetheart. Sounds good.” He turned back to you to smile. “I’ll be there.” He was really looking forward to Wednesday now.  He kept an eye on the guy as he walked on. He didn’t want him going back to bother you. 

You warmed at how he seemed protective. It was sweet. Now you couldn’t wait for Wednesday. Maybe you weren’t wrong in kinda crushing on him. He seemed to really want to hang out. Kevin came back, smirking as you blushed. 

“Did you say yes this time?” He asked. 

“I did. We hang out Wednesday.” You said softly. 

“Good.” Kevin beamed. 

“I’m not being silly?” You looked at him. 

“Silly?” He asked. “For saying yes? I think he really likes you.” He assured you. “Why would that make you silly?”

You gave him a look. “He’s out of my league.” You said simply. “Guys like him go for girls like Jess.” 

Kevin looked confused. “There’s not really a rule about that.” He blinked. 

“Okay, in my experience.” You countered. 

He shook his head. “He’s not out of your league, okay?” He gave your arm a squeeze. “You’re going to have a great time.” He smiled. “You deserve it.”

You repeated Kevin’s words as you locked up for the day on Wednesday. You were nervous, as it had been some time since you’d been on a date. Was this a date? Or just two people hanging out? Dean didn’t specify. And it would be way too awkward to ask! 

“Hi, sweetheart.” You heard Dean's voice, and turned to see him with flowers. He handed them to you shyly.

“Dean.” You gasped. “These are pretty.” You took them, smelling them. Okay, it was a date. That relieved you a bit. 

“Just like you.” He said sweetly. 

You blushed brighter, following him to his car. “What’s the plan for tonight?”

“Dinner and a Christmas movie?” He smiled. “I thought you’d enjoy that.” 

You nodded. “Love Christmas movies.”

“Did you want to drive to your place and drop off your car? Or I can drive us then bring you back.” He smiled. “Whatever you’d prefer.”

“We can just leave my car here and you can drop me back off here.” 

“Deal.” He held his door open so you could slide in. Conversation was light as he took you to another local food joint. He’d drove around to find the one he wanted to bring you to. If things went well, hopefully he could make you dinner some time. 

Once he parked, you giggled as he rushed around to open your door. “Careful, you’ll slip.” 

“Which I’d be completely embarrassed about.” He chuckled, offering his hand. He smiled as you took it. “I’ve been nervous all day.”

“Really? Me, too.” You admitted. 

“Really. Why were you nervous?” He asked, opening the door for you. 

“I…well…” You grew shy. “You’re out of my league.” You said softly. 

He blinked. “I’m out of your league.” 

You nodded. “Exactly.” 

“That’s not true.” He shook his head. “Not a bit. Does this have something to do with that jerk?” He got protective. “Was he a douche? I knew it.” He clenched his jaw. 

“He asked me out as a joke in high school. That’s all.” You shrugged. 

“What a dick.” He shook his head. 

You were sat at a table near the window. “It’s fine. It was years ago.” You smiled at the decorations. 

“Hate guys like that.” He looked over the menu. “Fought a few for picking on Sammy.” 

“Sam, who’s like half a foot taller than you?” You teased. You raised your eyebrow at him. 

“He used to be freakin’ small.” He huffed. “Was a punk.” He shook his head. “Mm, steak looks good.” He mused. “What sounds good to you?” 

“I love the pasta.” You admitted. 

“Want to share some bread?” He smiled. “Breads always the best.”

“Sure.” You smiled shyly. “Sounds good.” Hearing Jess laugh, you looked around. “Looks like Sam had the same idea!” 

Dean raised an eyebrow. He followed to where you were looking to see Sam and Jess.  “He didn't tell me.” He hummed. 

“Did you tell him you’d be going out tonight?” You blushed. 

“Yeah. He’d probably say I wouldn’t shut up about it.” He admitted, looking shy.

You giggled. “That’s sweet.” You told him as your waitress came to take your order. You both ordered happily. So far, you were enjoying your date. 

Dean ordered a brownie sundae to share. “I know this date isn’t over…but can we have a second date?” 

You smiled. “Yeah, I’d like that.” You nodded happily. You would be nervous to plan it. “I can give you my number so we can plan that.” 

“Sweet.” He looked so happy. “I’d really like that.” He held your hand as you two walked out after dessert. He had paid. He was already eager for the next date. 

Dean wrapped his arm around you at the theater. He smiled as you leaned a bit into him. You were so sweet. He felt brave and kissed the top of your head. 

You looked up at him shyly and kissed his cheek. You felt like punching yourself. 

He looked at you and winked. He hoped you were blushing. It was cute. He hoped to kiss you goodnight. You settled back against him happily. 

When the movie was over, he squeezed your hand gently as he led you back to the car. “I really liked tonight.” You beamed at him. 

When you were in the car, he cupped your cheek. “Can I kiss you, sweetheart?”

“Yeah.” You whispered. “You can.”

He dipped his head slightly and kissed you gently, stroking your cheek. He felt you smile into it. He parted his lips. 

Your cheeks were on fire. You kissed back shyly. His lips were so damn soft. You pulled back and blinked. Swallowing, you licked your lips. 

He winked. “Thank you.” He grinned as you giggled. “You’re so sweet.” He loved it. It was so refreshing. 

“Not as sweet as you.” You said softly. “You’ve been wonderful.” 

“Thanks.” He blushed as he drove. He’s never been called wonderful before. It made his insides flutter. “I’m really glad we had this date.” He couldn’t wait for the next one. “When are you free next?” He asked, already wanting to plan. 

You thought. “It might not be until after Christmas. The shop gets really slammed. Unless you don’t mind a later evening.” 

“I don’t mind. Just want to spend time with you.” He said easily. “Can I bring you dinner at work?” 

“Sure.” You agreed. “That would be nice.” You nodded. “Since you paid for this date, I can order us pizza for the next?” 

“Deal.” He agreed. “I’ll bring the drinks.” He promised. “Tomorrow?” He was eager to see you again. 

“Okay.” Was that too soon? You didn’t really mind. You liked his company. 

Dean kissed you once more before you went to your car. “Night, sweetheart.” 

“Night, Dean.” You smiled. “drive safe.” 

He nodded. “You, too.” He waited until you pulled away to head home. He was so excited that it went well. 

Dean grinned as you laughed. It was your third date at the shop and you both were playing cards. Hearing the door, you put your hand down. “I’ll be right back.” You chuckled. 

“Dean, Sam told us you’d be here.” 

You looked back at Dean. He looked surprised. “Mom? Dad?” He stood and came over. 

You blinked, stepping back. You hadn’t been expecting to meet his parents. Not this soon.

“What’re you doing here?” He asked.

“Wanted to come spend some time with you. Do a little Christmas together.” His mom smiled. “See your new place.” She went on. “Sam didn’t even mention us coming?” 

“No. At all.” He frowned. 

“He probably didn’t tell you on purpose.” His dad sighed. 

“Probably.” Dean shook his head. “Jerk.” He muttered. “Want my apartment key and I can meet you later?”

“Are you busy?” She asked. “We’d like to take you for dinner.”

“Yeah. Having dinner with Y/N.” He motioned to you. 

You gave a shy wave. 

Dean smiled before looking back at them before handing over his keys. “I’ll text you when I’m on my way.”

Mary raised an eyebrow before smiling. “Alright.” She took them. She smiled at you before leaving. 

You blushed and looked at him. “You could have gone.”

“I know, but…” He shrugged. “It’s our dinner night.” He said simply. “Sorry they just stopped by. I know Sammy did it on purpose.” He huffed. 

“It’s okay.” You said shyly. “They seem nice.”  

“They are. Mom’s cool. Dad’s…” He shrugged. “Manly.” He chuckled. “Rough.” He went back to eating take out. “They came a long way.” He told you. 

You nodded. “That’s really sweet. Maybe take them to the day before Christmas Eve thing?” You suggested. “Maybe they’d like that.”

Dean grinned. “Good idea.” He nodded. “I’ll mention it to them later.” He winked. He enjoyed how your blush deepened. It was adorable. “How did you want me to explain our situation to them? My mom will ask.” 

“How do you think you should?” You played with your sweater. You were curious what he would say.

“I can say we’re freshly dating?” He offered. “If that’s okay with you?” He looked at you. “I don’t want to say we’re just friends and I don’t want to pressure labels or anything.” He explained gently. He didn’t want to scare you off. He looked worried that you wouldn’t like what he suggested. 

You smiled softly. “I’m okay with that.” You agreed.  

“Great.” He breathed. He’d been worried you’d tell him that you weren’t dating. He was so serious about you. “Maybe soon I can call you my girlfriend?” 

You nodded automatically. “I’d like that.” You smiled as he looked so happy. He was a sweetheart. He made you feel so special. You hoped it lasted and he didn’t get bored. You worried about that. You were very different from each other. “Did you date before?” You asked, blushing. 

“Of course I’ve dated before.” He shrugged. “I’m sure you have, too.”  

You nodded. “Just a couple of times.” You explained. “Small town and all.” You reminded him. 

“Yeah, I get that.” He nodded. “Have I met anyone you’ve dated?”

You thought about it. “I went on a date with Kevin once.” You shrugged. “We both agreed we just liked being best friends.” 

“That makes sense.” He nodded. “You seem like good friends.” You had a lot in common. And got along really well from what he saw. He hoped he was interesting enough for you. Would you rather have someone more like Kevin? Someone who understood all about what you liked? He felt a bit worried about that. He glanced at your inventory. Maybe he’d have Sam buy him some books so he could learn. It would seem weird for him to buy them himself. 

You threw away the trash, pecking his cheek. “I hope you have fun with your parents.” You said sweetly. 

“Thank you, sweetheart. Maybe come to lunch with us tomorrow? Or is that too much?” He asked, kinda hoping that you’d want to join them. 

“If you want me to, I will.” You nodded. “I’m just shy around new people.” You chuckled. “I’m sure you could have figured that out.”

He grinned. “Yeah, it’s adorable.” He offered you his hand. 

You took it and giggled as he brought you close. Soft holiday music played in the back as he made the two of you sway. It was thankfully a slower night, so not many customers had come in. 

He grinned down at you, pecking your lips. “I’m glad I moved to town.” 

“So am I, handsome.” You smiled. “And that you lost that bet and had to get that fancy coffee.”  

He laughed. “Don’t tell Sammy.” He grinned. 

“I might. To see you blush.” You teased. “Because that’s cute.” 

He smirked. “Takes a lot for me to blush.” He told you, almost hoping you’d try.

“Oh?” You grinned. “Is that a challenge?”

“Maybe.” He smirked wider, squeezing your hips. “If that’s what you want it to be.” He flirted, bringing you closer and nipping your lip. “I’d like to see you try to get me to blush.” 

You chuckled. “Then I’ll let you borrow a book I got as a gag gift for Christmas last year…” 

He shook his head. “You can try.” He was curious about this book now. 

“Great.” You smirked. “What do I win if you blush?” You asked as he held you close.

He wiggled his eyebrows. “What do you want?” His voice was low. “Ladies choice.” 

You flushed. “Dinner at my place?” You asked, shyly. You were sure he was hoping for more. But, that’s what came to mind and felt right. 

“Deal.” He pecked your lips. “I’ll get the book from you tomorrow at lunch?” 

“Sure.” You giggled. “I’ll make sure to bring it.” It helped your nerves on meeting his parents. 

The next day, you locked up the shop for lunch, so nervous. You walked down to the diner, adjusting your jacket. The book was tucked into your pocket for him. You would give it to him after. 

Dean was waiting for you, leaning against his car. “Hey, beautiful.” He beamed. “How’s your day been?”

“Great, now.” You pecked his lips. “Been looking forward to seeing you.”

“So have I.” He pulled a candy cane out of his pocket and put it in your hand. “From the coffee shop.” He kissed your cheek.

You grinned. “I love these.” You wondered if you’d mentioned it to him. 

“I know.” He winked. He looked over as he saw his parents pull in. He held your hand in his, wanting to show you off. “Hi, mom. Hi, dad.” 

“Hey, Dean.” His dad nodded. “We didn’t officially meet yesterday.” He held out his hand. “I’m John.” 

“Nice to meet you.” You shook his hand. 

Mary offered a hug. “I love your hat.” She complimented you. 

“Oh, thank you.” You smiled, hugging her back. “Lovely to meet you.” You said happily. She was so nice already. Hopefully they’d like you. The four of you went inside and Sam stood, having been invited. “Hi, Sam.”

“Hey, Y/N.” He hugged you gently. “Glad you could come.” 

“Same here.” You sat by Dean. He put his arm around you, helping you relax a bit. 

Sam asked you how the store was doing. “Been busy?”

“It comes in bursts. I have a feeling Christmas Eve will be really busy.” You nodded. “Last minute gifts.” You chuckled. “I thankfully usually have help that day.”

“Do you like it?” Mary asked. “The shop?”

You nodded. “I love it. I look forward to owning it hopefully soon.” 

“That’s great.” Mary smiled. 

Dean smiled at you. “She’s awesome. Everyone here loves her.” He said happily. “She’s the sweetest.” He chuckled as you blushed. 

“No offense, but she doesn’t seem like the girl you usually see.” John spoke up. 

You blushed further but for a different reason. 

“You’re right. She’s different.” Dean nodded. “In a good way.” He said proudly. “Brings the best of me out.” He went on, surprising you. 

Mary beamed. “How sweet.” She gushed. 

Sam chuckled. “What have you done to my brother?” He asked teasingly. 

“I’m not quite sure.” You admitted. “I’ve just enjoyed spending time with him.” 

Dean grinned at you. “It’s been nice.” He said happily. 

John looked skeptical and wondered if Dean was just having some company for the holidays. That he’d call in January saying he broke up. He wouldn’t doubt that it was possible. He hoped that Mary didn’t get attached. Or Sam. He let out a sigh, knowing this wouldn’t go well. 

Dean ordered you a milkshake to share. It had become automatic for him. 

Mary beamed, happy to see her eldest so happy. She thought that you were good for him. He needed someone sweet in his life. She would worry a tiny bit less with you in the picture. 

“I don’t think we should get attached to her, Mary.” John told her as they pulled out of the parking lot.

She looked worried. “No? You didn’t like her?” She asked, looking at him. “I like her. She’s sweet.”

“Since when has Dean brought home someone like that?” He pointed out. “I can’t see them lasting much longer than New Year’s.” 

Mary made a noise. “Maybe she’s different for a reason.” She pointed out. “And maybe that’s a good thing.” 

John shrugged. “He’s going to break that poor woman’s heart. That’s all I’m sayin’.” He shook his head. 

“Don’t tell Dean that.” She said firmly. “I think he really cares for her.”

“Or her company.” He countered. 

“John.” She sighed. “I don’t think that’s it.” She was sure. She saw something different when her son looked at you. And she would be damned if her husband ruined it.

“You don’t think he’d go back to Cassie or Lisa if they came around?” He mentioned as they drove. “In a heart beat. This one owns a comic book store, Mary. That’s Sam not Dean.” He pointed out seriously.

Mary sighed. “We will see.” She told him simply. She was not in agreement. At all. She felt hopeful. She would tell Dean how excited she was before they left. She hoped that maybe they could see you again before they left after Christmas. You were kind. 

“That went well.” Dean grinned, standing with you by the Impala. “Really well actually. Think my mom loved you.” He chuckled. 

You smiled. “I hope so. I don’t think your dad did, though.”

“He’s like that.” He shrugged. “I wouldn’t worry about it.” He kissed your cheek. “How about tonight we go riding around to look at the lights?” He asked. “Get some hot cocoa for it?”

You grinned. “Sounds fun.” You nodded. “I’d like that. Come get me when I close the store? And until then…you can start this.” You giggled, pulling out the book.

He brightened and looked at it eagerly. “So, this was a gag gift?”

You nodded, cheeks red. “Yeah, last Christmas.”

He chuckled. “Classic.” He grinned. “Have you actually read it?” 

“Not really, no.” You admitted. “It didn’t seem like my kinda book.” 

“No?” He wiggled his eyebrows at you. “Not even a little?”

You shook your head. “Nuh uh.” You told him honestly. 

He chuckled and looked through it. “I’ll let you know what I think.” He winked before putting it in his back pocket. “See you soon, sweetheart.” He leaned down and pecked your lips. 

“See you soon.” You pecked his back. You went back to work, a smile on your face. You really hoped that things kept going well.  Dean was amazing. 

Dean couldn’t stop smiling as he drove home, either. He loved your dates. He decided to officially ask you to be his girlfriend that night. 

Dean parked at a nice little clearing where you could see some houses with lights. It was romantic. He squeezed your hand and looked at you. You smiled over at him. 

He leaned over and kissed you gently, stroking your cheek. “I have a question.”

“Yeah?” You wondered what it was. 

“Would you like to be my girlfriend?” He smiled. 

You gasped, shocked. “Really?” 

He nodded. “Yeah, really.” He chuckled. “I’d love to be your boyfriend.” 

You warmed. “You’re sure?” 

“I’m sure. Why do you keep asking?” He furrowed his brows. 

“I just know I’m not your type.” You whispered. You looked down. “What if the novelty wears off?” 

“Well, I doubt that.” He said easily. “I really like you.” He shrugged. “I doubt I’m your type either.” He pointed out gently. “Right?”

You blushed before nodding. “Because I would think that you’re out of my league, and all that.”

He kissed your forehead. “But you really like me right?” 

“I really do.” You said softly, smiling as he kissed you. His kiss was soft, and sweet. 

“Good, then can we be together?” He mumbled. 

“I’d like that.” You said softly. 

He smiled and kissed you again. He was so happy! He deepened the kiss in excitement. You were his girlfriend. 

You made a noise and moved closer to him. You put your hand on his chest as you did.  He was such a good kisser. 

After a few, the two of you pulled away for air. He grinned at you. “More lights?” He asked. 

“Then maybe get a snack?” You smiled. 

“Sounds good.” He nodded. It was turning into an amazing night. He drove off, holding your hand again. The two of you talked about anything. He never felt like he had to hold back. You never ever judged. He loved that about you. It was refreshing. 

You texted Dean Christmas morning, since you wouldn’t be seeing him. Merry Christmas! 😘 You sent him, smiling. 

He sent you a selfie with his Christmas sweater. Merry Christmas, sweetheart 😘 

So handsome :) You complimented him. You shyly took one to send back. 

Beautiful 😍 😍😍😍 He complimented you. 

Enjoy your Christmas with your family! You hoped to see him soon. Maybe get a New Years kiss. That would be so sweet! Your first New Years kiss! 

You yawned as you cuddled up on the couch that night and saw your phone light up with Dean’s call. “Hi.” You answered. “This is a nice surprise.”

“I have an even better one.” He chuckled. “I’m parked in front of your place. Can I come in?” He asked.

That perked you up so you rushed to the door. “Yes!” 

It didn’t take him long to get to the door and he beamed when he saw you. “Merry Christmas, babe.” He hugged you close. 

You made a happy noise, so excited to see him. You instantly hugged him back. “I didn’t think I’d see you until maybe New Years.”

He cupped your cheek. “Had to give my girl her present.” He said as you let him in, where it was warm. 

“You didn’t have to get me anything.” You tugged him to sit. 

“It’s not big.” He promised, handing you a small gift bag. “But I hope you like it.”  

You kissed his cheek and eagerly opened it. You felt bad you hadn’t gotten him anything. You gasped at the desk calendar that had a scene and quote from your favorite movie each day. “This is amazing!” 

He beamed. “I was worried you had something like it.” He admitted shyly. 

You hugged him. “Nope. And it’s perfect for the new year!” You kissed his cheek. “I’ll put it on my desk.” 

He smiled. “Great.” He hugged you tight. 

“Do you want to stay for a few?” You asked. “I can make you a nice drink? Hot cocoa with marshmallows?” You smiled. 

“Like I could turn that down.” He kissed your cheek and took off his jacket and boots while you went to do that. He looked around, as it was his first time in your apartment. He smiled at your decorations and pictures. It felt very you. 

You brought out a mug for him, with a small plate of cookies. “How was your day?”

“Nice. It was good to have the family together.” He ate a cookie happily. “Mom baked a pecan pie, too.” He grinned. “Missed them.” He chuckled. “How was yours?” He sipped his drink. “Hopefully festive.” He could tell you really loved Christmas. 

“It was good.” You got comfortable next to him. “Spent the morning with my dad, dropped off Kevin’s present and saw his mom.” You told him, smiling. 

“What’d you get Kevin?” He grinned. 

“A dungeon master shirt, a new set of dice, and then some lounge pants.” You chuckled. 

“Fancy.” He chuckled. 

You sipped your hot cocoa, smiling. This was a perfect ending to your day. You had been contemplating going to bed minutes before he called. Now you got cuddles. “What did you get for Christmas?”

“Ma got me clothes.” He chuckled. “Jeans and stuff. Always needed.” He shrugged. “Sammy got me a nice picture frame to hang up on my bare wall.” He was amused. “He also got me some of my favorite whiskey but that was before mom and dad showed up.” 

“What’s your favorite?” You looked up at him. 

He told you his favorite brand. “But I’m okay with anything.” He shrugged a shoulder. 

“I’ll keep that in mind.” You smiled. “I’m not a big drinker. I don’t have anything against it, and I’ll have a drink or two with dinner, or with friends, but not enough to have a favorite.” 

He kissed your head. “That’s okay. Anytime you want me to bring anything, let me know.” He smiled as you leaned into him. He enjoyed spending time with you. “Is there anything you’d like to try?” 

You shrugged in thought. “I guess anything you like.” You told him. “Or anything you think I may like?”  

“You’d probably like something sweet.” He nodded. “Or wine.” He mused. “We’ll find something you like.” He promised. 

“You just wanna see me tipsy.” You teased. 

“Maybe.” He winked. “That would be amusing.” He chuckled. 

You blushed slightly. “Maybe.” You sipped your drink. You two were pretty different in your tastes. But somehow, that worked. 

He set his mug down and brought you onto his lap. “Do you have plans for New Year’s?” He thought you may have plans with Kevin. 

“Not many at the moment.” You admitted. “You? Going out with Sam?”

“I think he’s going out with Jess.” He nodded. “He goes back to Stanford the second, though.” 

“I’m glad they hit it off.” You smiled. “They seem to really like each other.” You looked at him. “I thought you liked her.” 

He looked at you. “You did?”

You nodded. “Yeah.” You said shyly and blushed as you looked down. You explained why. 

He shrugged. “Yeah, I guess I can see that. I thought Sam liked you.” He admitted. “Like, instantly.”

You blushed brighter. “Oh. I doubt that.” You shook your head. 

He blinked. “Why not? You’re exactly his type.” He pointed out. “You’ve got a lot in common.” He motioned. “He’s nerdy, too.” He went on. 

You looked down. “Oh. Well…” You shrugged. “Him and Jess seem to have a lot in common, too.” You noted. “She’s happy to be seeing him.” You were glad your cousin was happy. 

Dean nodded and kissed your head. “I had been worried I wouldn’t get a chance to ask you out before he did, honestly.” He admitted. “Kind of told him to back off. Just a little.” 

“You did?” You blinked, looking at him.

He nodded sheepishly. “Told him he lives too far from here.” He licked his lips. “Even though him and Jess will probably make it work.” He really saw them doing whatever it took.

“They probably will.” You agreed. “I hope they work out.”

“So do I.” He nodded. “I know you and I will.” He grinned. 

“Yeah?” You smiled. “How do you know?” 

He cupped your jaw. “Because the second I laid eyes on you at that coffee shop, I knew we were meant to be.” He said softly. “I had to know you. I did ask about your coffee, and your beanie. Most basic conversation starters ever.” 

You warmed, still in disbelief that you caught his attention. He could have his choice of anyone. 

He kissed you softly and smiled. “Maybe we can have a sleepover soon? It can be completely rated G!” He added quickly, not wanting you to think the wrong thing. 

Your ears turned red. “Yeah, we can do that.” You agreed. “Maybe after New Year’s?” 

He nodded. “Works for me.” He smiled. “We can do a movie night or something.” He said happily. “Get snacks and all that.”

“Perfect.” You hugged him. “It’ll be fun.” 

Kevin texted you a couple days after Christmas. Hey, last minute party, you in? And Dean? He asked. 

I can ask. I don’t know if he has plans.

Okay :) let me know. 

You pulled up your texts with Dean. Kevin invited us to a last minute party. Would you like to go? 

Hell, yeah. Can Sammy come? He asked. 

I can’t see why not. Jess will probably go. You told him. I can give you the address to meet me there? 

Or I can pick my girl up :P 

You giggled sheepishly. Okay fine :) You agreed before going to get dressed. You wanted to look nice for Dean. He hadn’t really seen you dress up for a party yet. You sprayed on your perfume just as he texted he was there for you. You hoped that he liked the outfit that you picked.

He licked his lips as you got in. “You look hot, babe.” He grinned. 

“Even with my coat?” You giggled. 

He nodded. “Yeah, can’t wait to see without.” He said as he drove. “I brought drinks. Didn’t want to show up empty handed.” He chuckled. “Don’t wanna be rude.” 

You grinned. “You’re sweet.” You wondered how many people were going. “I’m guessing Jess picked up Sam?” 

He nodded. “She’s excited.” 

You chuckled. “She was the partier of the two of us in high school.” 

“I can see that.” He chuckled. He leaned over and kissed you once he parked. “Wanted that before we go hang out.”

You grinned. “Thanks, handsome.” You followed him inside once he got the bags. “Hi, Kev.” You went to hug him. 

He hugged you. “Hey, so glad you guys made it.” He grinned. He shook Dean’s hand and motioned to where he could put the drinks. 

“Of course, man.” Dean set the bags down. “Thanks for the invite.” 

“The better Winchester is here.” Sam said as he came in with Jess. 

“Oh, your mom is here?” You asked playfully. Both guys gasped, making Jess giggle. She nudged you gently. 

“Well, you’re probably right.” Dean caved. “She’s the best.” 

“Awe, momma’s boy.” Jess chuckled. She thought it was cute. 

Dean grinned. “Yeah…” He nodded, slipping his arm around your waist. He kissed your temple as more people arrived. He smiled as you waved and greeted most. Sam brought over a drink for him. “Thanks, man.” He sipped it. 

Jess brought you a hot chocolate. “Figured you weren’t drinking.” 

You shrugged. “I could try a bit?” You looked at Dean.

“Course, sweetheart.” He smiled. “Drink whatever you’d like, okay?” 

You nodded and followed Jess while the brothers mingled. “I hope you aren’t drinking to make Dean happy.” She told you once you were at the drinks. 

“No, not really anyway. He asked me what I like, and I don’t know enough to know.” You admitted. “I’d like to at least have an opinion.”

She nodded. “Just be careful. I know you two are the opposites.” She said gently. “I don’t want to see you getting hurt.” 

“He’s nice. Sweet. Doesn’t judge…” You told her. “I really like him, and I feel he really likes me.”  

She nodded. “I’m happy for you.” She said softly. 

“Thank you.” You smiled. “How’s Sam?” You asked, changing the subject. 

“Amazing. He’s so sweet!” She grinned. Her eyes went back to Sam. “And smart.” She added. 

You grinned. “I’m glad you two hit it off.” You loved seeing her so happy! 

She giggled. “Thank you.” 

After a few minutes, you and Jess made your way back to the guys. Dean was leaning against the wall and someone was very close as they talked to him. You blinked, noting he didn’t mind. 

“Is that Daisy from the book store?” Jess frowned. 

You nodded. “Yeah, it is.” You sighed, looking down at the drink in your hand.  You heard her laugh so you peeked up again, scrunching your nose. Sipping your drink, you went to talk to Kevin. 

Jess went to stand with Sam, but not before sending Dean a look. She was not happy with him. “Flick your brother for me.” She asked Sam. 

He did so, easily. 

“Dude.” Dean frowned at him. “The hell was that for?” 

Sam and Jess sent him another look. “Where’s your girlfriend?” Sam asked. He raised his eyebrow at his brother. 

“She was with Jess. Did she go to the bathroom or something?” He asked her.  

Jess pursed her lips. “No, she’s with Kevin.” 

“Want another refill?” Daisy asked Dean. “I can get us each another drink.” 

Jess smiled sweetly at her. “Yeah, why don’t you go do that?” Her smile fell when she walked away. “What gives, Dean? Letting Daisy hang off your arm like that?” She asked, annoyed. “All flirty?!”

Dean huffed. “We were just talking.” He rolled his eyes. 

“Not what it looked like.” Sam frowned. “At all. Looked like you’d be telling me don’t wait up.” 

“As if.” Dean scoffed and went to find you. “Hey, babe.” He smiled. “Did you find a drink you liked?” He asked, putting his arm around you.  

You nodded. “Jess made it for me.” You said quietly. “It’s good.” 

Kevin squeezed your shoulder. “We’re gonna set up some water pong.” He smiled. “Come join us?” 

You nodded. “We’ll join.” You didn’t want to ruin Kevin’s mood or anything. That wouldn’t be fair. 

Dean watched him walk away and kissed your temple. “So, what did she make you?” 

“Dean, you left without your refill.” Daisy came up.

“Oh, thanks.” He grinned and took it. “Appreciate it.” He clinked his glass with hers. “I’m sure you know Y/N, but I’d like to introduce you to my girlfriend.” He beamed. He sounded so proud. 

Daisy looked a bit surprised. “Oh, I didn’t know you were seeing someone.” She tilted her head. “You didn’t make it seem like you were. I was sort of coming on to you?” She said honestly. 

You looked down, sipping your drink awkwardly. 

Dean blinked. “Oh. I’m sorry.” He shook his head. “My bad.” 

Daisy nodded and looked at you, then back to him. “Yeah, your bad.” The two of you weren’t close but she wouldn’t have actively flirted in front of you knowing you were together. That just wasn’t how she was. She gave you an apologetic look before she left. Hopefully you didn’t hate her or anything like that now. She’d come to your store to apologize at some point. 

The two of you were left in an awkward silence. “I’m sorry.” Dean looked at you. “That wasn’t my intention.” He assured you. 

You shrugged. “It’s fine.” You brushed it off. Was it something you’d have to get used to? You weren’t sure you liked that. 

Dean chewed on the inside of his cheek. “It’s not, and I’ll work on it.” He promised. “I should have told her I wasn’t interested.” He shook his head. “I’m an ass for that.” He didn’t like that he’d made you upset. 

“Will it happen a lot?” You asked softly. You glanced at him. “Because if it will, I don’t want this.” Your voice wavered. You hated saying it, but you had boundaries. 

“It won’t happen a lot. I can’t say I won’t be approached, but I promise to not do that.” He didn’t want to lose you. 

You looked down again and nodded. You’d just have to hope that was true. 

“Let’s go. I’m great at this game.” He smiled. He hoped that he could take your mind off of this. He felt so bad. “Maybe we can get an uber back to your place and have that sleepover after?” 

You blushed. “Sure.” You nodded. Maybe that would help. 

Dean grinned when you agreed. He hoped that meant you trusted him again. “How late is pizza delivery here?”

You automatically giggled. “Eleven. Not twenty four hour unfortunately.” You told him. “Why?” 

“Pizza is always a good choice.” He grinned. “Was gonna get us some.” 

“There’s nachos.” Kevin spoke up. “And other things in the kitchen.” He motioned. “Help yourself.” 

You smiled softly. “We’ll play a round then go get a snack?” You suggested to Dean. 

He nodded. “Let’s kick some ass.” He pecked your lips. The two of you joined the game and soon everyone was having a great time. He loved hearing your laughter. It was the best. 

Dean scooped you up after he’d ordered your Uber. “C’mon babe.” He smiled. “Let’s get our cuddling started early.” He kissed your cheek, making you giggle. You'd been drinking and extra giggly. He knew you’d be a lightweight when it came to handling your drink. And that you’d be adorable.  

“Dean!” You giggled as his stubble tickled. 

“Yes, beautiful?” He grinned. 

“You’re silly.” You leaned your head on his shoulder. “And you smell good.” You complimented him.

He chuckled as he got you in the Uber. He made sure you were safely buckled, as well. He grinned as you kissed him in thanks. 

Jess sighed as she watched you leave with Dean. “I’m sorry, but I don’t think they work well together.” She looked at Sam. “He’s going to hurt her.”

Sam sighed. “It’s hard.” He nodded. “But I can tell he really likes her.”

“You know she’s not his type.” She pointed out. “I barely know him and I can see that.” 

Sam groaned. “I know.” He nodded. “I’m hoping they last.” He said truthfully. “She makes him happier than I’ve seen in a long time.”

“Will he get tired of her?” She asked softly. 

“I’d hope not.” Sam looked at her. “But only time will tell.” He brought her close. “Your place?” He asked, changing the subject. 

She pouted and poked his chest. She was still worried about you! “Focus!” She told him, making him raise an eyebrow. 

“I’ll talk to him.” He kissed her cheek. “I promise.” He hugged her. “Us time?” He asked, hopeful. 

“Fine, just because you’re so cute.” She flirted. 

He grinned and followed her out. He wasn’t looking forward to saying goodbye in a few days. He really, really liked her. He hoped they could keep seeing each other. That she wouldn’t get tired of the distance. He kissed her cheek gently once he could. “Be mine?” He asked, sounding shy. 

She grinned. “Awe, Sam!” She gushed. “Yes!” She kissed him. “I would love that!” 

He lifted her in excitement. He was so glad she had said yes. He’d worry about Dean later. Right now, he was focused on her. He kissed her softly once they got into an Uber. 

Once they got to your place, Dean laced his fingers with yours. He kissed you softly once you both warmed up. “I’m glad you agreed to me staying over.” 

You grinned. “I bet you’re cuddly in bed.” You wrapped your arm around him. 

“I am a great big spoon.” He grinned. 

You giggled and tugged him to get ready for bed. “I’ll make us breakfast in the morning.” 

“Sounds great, sweetheart.” He kicked off his jeans. “As long as next time I get to cook for you.” He slipped off his button up. “Deal?” He asked you. 

“Deal.” You shyly changed.  You wore some fluffy pajamas. You hoped that he didn’t mind your choice of attire. 

He pulled you close once you both got under the covers. He wondered if he’d wake up in his own bed, alone, and that this would be a dream. He couldn’t believe he was here. He kissed your cheek happily. “Night, babe.” He said softly. 

“Night.” You said softly. “Sleep well.” You couldn’t believe you were cuddled up to him. And that he was holding you close. You hoped for many nights of this. 

Dean woke up to the smell of breakfast the next morning. He smiled widely to himself. Stretching, he got out of bed to go find you. “Hey, beautiful.” He beamed. 

You looked over at him from where you were working on breakfast. “Hi, handsome.” You loved his bed head. “You look adorable.” You giggled. “I hope you slept well.” 

“So well.” He hugged you. “How about you?” 

“Great.” You kissed his jaw. “Breakfast is almost done.” 

“What can I do?” He wanted to help, even if that was doing something small

“Juice from the fridge?” You suggested. “Also, do you have work today?” You asked him, looking back to the pan.

“This afternoon, yeah.” He nodded. “I’ll have to Uber back to get my car first, though. And get home to shower and change.” 

“I can drive you?” You offered. “So you don’t have to pay another Uber? I can bring you before I head to work.” 

“Sure.” He grinned. “I won’t turn down more time with you.” He winked and set the table with your drinks. He watched you plate breakfast before coming to the table. He liked this domestic feeling. Which was new to him. He wasn’t quite used to having a girlfriend. “Do you have plans for New Year’s?” 

You shook your head. “No. You?” You sipped your juice.

“Nah.” He smiled. “Wanna go out?” He asked, hopeful. “Our first new year’s.” 

“I’d love to. Not many places are open that late here, though.” You warned him. “Maybe one bar?” 

“What if we go to the big city?” He asked, starting to eat. “Have a nice date night? Get a hotel room?”

You warmed. “That’s a big date.” You noted. 

“I know but I think we’re pretty serious about each other.” He felt they were. Was he thinking wrong? 

“Can I think about it? I’ve never really gone to the big city…” You admitted. 

He nodded. “Of course.” He didn’t want you feeling forced. He felt it would be a great date. “If not, we can do something here.” He assured. “Have our own party.” He went on. “Get snacks, pizza, stuff like that.” 

“That sounds good too.” You smiled. “I’ll let you know.” After all, New Years was only a couple days away. You could try the fancy date. That seemed to be something that he was into. You wanted for him to enjoy it. Would he be bummed if you said you wanted to do it at home? You watched him as he happily ate breakfast. “We can do the hotel.” 

“Really? You’re sure?” He asked. “I don’t want you to feel forced.” He offered his hand. 

You took it and smiled as he tugged you on his lap. “I’m sure.”  

He kissed your cheek. “Okay, we’ll plan it.” He said excitedly. He couldn’t wait to go out with you. He planned to spoil you. You deserved it. Kissing your shoulder, he fed you a bit of bacon. He grinned as you giggled. “I love that sound.” 

You smiled and leaned into him. 

You tugged your sweater down as you walked through the busy street with Dean. He had planned everything, and you told him that you wanted to help pay for something. He was so excited. It was adorable. He was holding your hand happily. 

You stopped at a restaurant. “Can I buy dinner?” You asked. 

“Sure, babe.” He chuckled. 

“Thank you.” You grinned and tugged him in. You looked forward to this entire date. 

Dean followed the hostess to a table. Everywhere was pretty packed. He kept you close. He was excited to show you off. You were his girlfriend, and he was proud. “Have I told you how beautiful you look?” He asked as you reached the table.

Your hostess grinned at you. “You have a sweet one.” 

You blushed and nodded. “I do.” 

She winked at you before leaving you be. Dean pulled your chair out for you. He kissed your shoulder once you sat. 

“Thank you.” You smiled and glanced around while he sat. You weren’t used to so many people. He seemed at ease, though. “Did you grow up in a big city?” You asked as you looked over the drink menu.

Dean shrugged. “Probably average.” He motioned around. “Not this big, but not bad. Not as small as your place.” He grinned. 

You chuckled at that. “Yeah, I’m sure.” You decided to order some wine. “I’m looking forward to kissing you at midnight.” 

He beamed. “So am I.” He looked like a kid on Christmas. He couldn’t believe he was out with his girlfriend! Their first new years together. He smiled at you, making you nudge your foot against his. He chuckled. “Playing footsies?” 

“Stopping you from making my face cherry red.” You giggled. “That’s all.” 

He smirked. “Oh, so I should stop flirting?” He asked playfully. 

“No!” You said quickly. “Don’t want that.” You shook your head. 

“Fine.” He chuckled. “I won’t stop.” He sipped his drink once you got them. He winked as you as you glanced at him while you sipped your wine. “Is it good?” 

You shrugged a shoulder. “Not as fruity as what Jess made me.” 

“You like fruity?” He looked through the drink menu. “We can get you something else.”

“After this.” You smiled. “I’d like to at least finish this.” You sipped at it. 

Dean grinned, happy you were having a good time. “Sounds good, sweetheart.”

“What’s our plan after this?” You grinned. “If you had one.”  

“I was thinking of trying a club or a movie.” He suggested “But you don’t seem like the club type?” He noted. “So, catch a movie?” He went on, planning as he spoke. “And if we have to wait a bit for it to start, most theaters have an arcade we can play in.” 

You sipped your drink. “If you prefer the club, we can try?” You offered shyly.

“No, it’s okay sweetheart.” He smiled. “I don’t want you to be uncomfortable.” He shook his head and pulled up the movie showings. He started listing off movie names. He picked the one you lit up at. He hoped to always keep you smiling. He’d do anything to do that. He loved your smile. “Great, so our night is set.” He said happily. “Then we can ring in the new year in the room.” He beamed. “Enjoy our time together.” He couldn't wait to hold you again. 

You smiled to yourself, enjoying dinner. “I’m glad you suggested this.” You told him. “It’s been nice getting out and doing things we haven’t before.” You said cheerfully, hoping it wasn’t the magic of the holiday making him want this. That he would end it at the end of this. You pushed that worry down for the time being.  “What’s your brother doing tonight?” 

“Spending it with Jess. He leaves tomorrow.” He noted. “He’s sad.” He sighed. “Mopey.” 

“Awe. At least they can facetime?” You offered. “They’re close. She’ll visit when she can.” You assured him. 

Dean nodded. “They’ll make it work. He’s already head over heels.” He chuckled. “Like in deep.” 

“That’s sweet.” You giggled. “I think Jess is too.” You said honestly. 

“Good to know.” He nodded. “I worry about him.” He admitted. “Don’t want him hurt.” He said softly. 

You softened. “That’s sweet.” You hoped they worked out. You wondered if Sam worried if you’d hurt Dean. You figured he did, and looked down. You wouldn’t do that. Ever. 

“What’s wrong?” He nudged your foot gently. “You got sad eyes.” He noted. “Did I say something?” 

You shook your head. “Just thinking that Sam probably worries about me hurting you.” You admitted. 

“Oh.” He said softly. “He shouldn’t worry about that.” He shrugged. 

“I’m sure he will no matter what.” 

“Brothers.” He shrugged again, looking excited when the food came. “Want to try a bite of mine?” he asked you.  When you nodded, he beamed. He fed you a bite happily. 

You smiled when you finished your bite. “Wow, this place is really good.” You gushed. 

“You picked great.” 

“Want to try mine?” You offered him a bite, which he happily took. You giggled at the face he made. “Good?” You asked. 

He nodded quickly. “We’re so coming here again.” He said once he’d swallowed. “So making a plan for another date night like this.” 

You grinned. “Deal.” You agreed. 

Dean set up the ball drop show on tv. You both had changed into your pajamas, and he thought you were beautiful. He cuddled you close and rubbed your arm. “So soft.” He kissed your cheek. 

“Maybe next time I can borrow one of your shirts to sleep in?” You asked shyly. 

“Of course.” He played with your hair. “You could take mine right now, even.” He kissed your jaw gently. He wrapped his arm around your waist, holding you close. 

You played with the neckline of his shirt. “Okay.” You whispered. You watched as he sat up and pulled his shirt off over his head easily. You flushed brightly as he handed you his shirt but you didn’t do anything with it as you kissed him softly. You cupped the back of his head as you did. 

Dean held back as he kissed back, gently holding you close. He didn’t want to pressure you in any way. He groaned when you settled on his lap. “Sorry.” He mumbled. 

“Why?” You asked, hands on his shoulders. 

“Don’t want to make you uncomfortable.” He rested his hands on your thighs. “That’s all.” 

“You’re not.” You kissed his jaw and down his neck, hearing him suck in a breath. “If I was, would I be doing this?” 

“Guess not.” He tilted his neck. His voice was low as he closed his eyes. “Feels nice.” He ran his hands up your thighs to your hips. The both of you got braver with each other. You enjoyed feeling his chest under your fingers. 

“Can we?” You asked softly. 

“Can we what, sweetheart?” He didn’t want to jump to conclusions. 

You grew shyer and kissed his shoulder. “Be together?” You rocked your hips. 

Dean groaned again. “You’re sure? Positive?” He pulled back to look at you. You bit your lip and nodded. “Is…is this your first time? Just so I know?” 

“No.” You shook your head.

He stood and set you down before going to get protection. He was excited to make this a great night for you. He groaned when he turned back to you and you’d taken off your top. “Sweetheart…” He breathed. 

You blushed. “What?” 

“You’re beautiful.” He came over quickly. He leaned over you, kissing you. He cupped your face happily. He hadn’t expected you to want to sleep together yet, but was glad he came prepared in case. 

You felt confident taking this step with Dean, and it made it even more special that it was on this date. You leaned back, pulling him with you. 

Dean smiled against your lips, just as excited. 

After that night, the two of you felt even closer, which made your heart soar. You held hands the entire way home. You were already looking forward to your next date. “Best New Years, ever.” Dean smiled as he parked in front of your place. 

“I happen to agree.” You grinned. “Thank you.” You pecked his lips. “Want to have lunch on Wednesday?” You asked. “We can get something and play board games at the shop again?” 

“Sounds perfect.” He agreed instantly. “I’ll get us subs, you get us drinks?”

“Deal.” You agreed. “See you then.” You leaned over and kissed his cheek. “It’s a date.” 

“Bye, babe.” He waved happily. 

“Bye, handsome.” You waved before getting out. He had completely made your night and day. You couldn’t stop smiling. You’d spend the rest of the evening relaxing then get ready to open up the shop again tomorrow. 

Dean waited until you were inside to pull away. He grinned to himself all the way home. 

Jess glanced to the booth before glancing down at her notepad then back again. Was that Dean? It looked like him. But you worked today through lunch, so who was he meeting? She wondered if she should go say hi. He wasn’t in her section, but still. They were friends, right? She walked over. “Dean!” She smiled. “Wanted to say hi.” She told him. 

“Hey, Jess.” He smiled back at her. “What’s up?” 

“Slower day.” She shrugged. “People still on winter break. You? Lunch alone?” She wondered, as he normally only came in with you.

“Not today. Old friend is driving through, wanted to catch up.” He nodded. “Figured the diner would be a good place for that.” 

“Oh, cool.” She nodded. “Well, enjoy that time with him.” She said sincerely. 

“Dean?” Came a woman’s voice. 

Dean turned and grinned. “There she is.” He stood. 

Jess stepped back and blinked. Did you know Dean was meeting up with her? Was she overreacting? She didn’t want to place a worry in your head. “Enjoy your lunch.” She said before heading back to her section. She couldn’t help but glance at them often. They looked really happy to see each other. She chewed on her lip as she went. 

You were locking up when Jess called you. “Hey, cousin.” You answered happily. “It’s sort of late, everything okay?” You asked, hoping she was just wanting to say hi. 

“Have you talked to Dean today?” She asked casually. 

“We’ve been texting on and off, why?” You went to your car. 

She stayed quiet. “Just wondering. I ran into him earlier at work.” She explained. 

“It is a small town, with limited places to eat.” You chuckled. 

“Yeah, you’re right.” She laughed softly. 

“You just called to say you saw Dean?” You found that strange. 

She sighed. “I’m sorry. I’m being weird. He had lunch with some lady and I freaked out for you.” 

“Some lady?” You asked, getting into your car. “His mom left, so I know it wasn’t her.”  

“I didn’t get a name. Dark hair?” She offered. 

You thought for a moment. “No idea, honestly. He hasn’t mentioned anything.”

“It’s honestly probably nothing.” She noted. Did she just call you for nothing? 

“No, I know you felt something if you needed to call me.” You told her. “Thank you for looking out for me either way. I’ll text him later to ask how his day went. See if he mentions her.” 

“Okay.” She let out a breath. “Sorry!” She hoped it was nothing.

“It’s okay. I’ll text you.” You hung up and shrugged to yourself as you text Dean. Finally out. How’re you? 😘 You left your phone on your lap as you started your car, eager to get home. You hoped to have a reply when you got inside. 

Dean grinned when he saw that you texted. Hey, babe! :) He sent back instantly. Miss you. Can’t wait to see you tomorrow. 

A little bit later, you texted back. Miss you, too! How was your day? 

Alright. Slow day. He sent back. How was the shop?

Decent. The usual :) You answered. Tired now. 

Hopefully you can get some relaxing in now :) run a nice bath. He suggested. Sleep well, babe. He added. 

You were a bit surprised that he pretty much ended your conversation. He usually texted more. Sighing, you made your way to your room to change. What if he was with someone? You chewed on your lip, wondering why he didn’t bring her up. You pulled up your texts. Want to join me for a slice of pie and some hot cocoa? 

What kind of pie? ;) 

You couldn’t help but chuckle at that. Well, we can start by finishing off the pecan pie I have ;) 

Say no more. I’ll be there in twenty. He sent you quickly.

He only lived five minutes away but you didn’t focus on that. You quickly pulled on the shirt that he’d given you to borrow. You went to start making some hot cocoa. 

Finally, there was a knock on your door. You rushed to open it and smiled as he hugged you. “I’m glad you came over.” 

“So am I.” He lifted you as he stepped in. He kicked the door shut once he was in. “Smells good.” He pecked your cheek.

You squeezed him and looked up at him. “I’ll heat up that pie for us.”  

He kissed you softly. “Okay.” He let you go, enjoying how you looked in his shirt. “You’re hot.” He winked. 

“So are you.” You blushed. 

He squeezed your hip and sat while you warmed up the pie. He enjoyed the peacefulness he felt when he was with you. It made his day better. 

“Do you have plans tomorrow?” You asked, glancing at him. 

“Just our date.” He winked. “Can’t wait.” He said truthfully. 

Should you mention Jess seeing him? You chewed on your lip. “Jess mentioned she saw you today.” You told him as you set his plate and mug on the table.  

“Oh at the diner? Yeah she wasn’t in our section today.” He nodded. “She was nice enough to come say hi.” 

You sipped your mug as you sat. “Did you have lunch with someone?” You asked casually.  

He frowned instantly. “What?” He stared at you. “Did Jess say something?” 

You chewed on the inside of your cheek. “She mentioned it.” You nodded. 

Dean focused on his pie, brows furrowed. What did Jess tell you?

You could tell he didn’t look pleased. “Forget I mentioned it.” You didn’t mean to upset him. 

He shook his head and sipped his drink. “Jess always going to be spying on me?” He asked. 

“She wasn't spying.” You regretted saying anything. “She just mentioned it during a conversation. I promise she’s not spying.” You assured him, hoping he wasn’t mad because he was hiding something. 

“She did come over to just say hi.” He dropped his shoulders. “I do normally only go with you.” 

You nodded. “Jess isn’t like that.” You promised. “Never has been.”  

“Good.” He finished off his pie. “That was good, babe.” He went to rinse off his dish. His phone went off as he did. He went to answer it as he finished his cocoa. “Hey.” He said simply. “Yeah, I’ll be home soon.”

You looked at him at that. It was late for someone to go by. You focused on your own food. 

“See you then, bye.” He hung up and kissed your cheek. “Thanks for the mini date, sweetheart.” He smiled. “It’ll hold me over until tomorrow.”

You nodded. “Yeah.” You said softly. “Thanks for coming.” You gave him a small smile. 

He pecked your lips. “I’ll text you in the morning.” He said before heading out.

Once you heard the door shut, you sagged. Not only did he not answer your question, he left you with more. Were you overthinking things? Was he seeing someone else? Why didn’t he tell you? If it was some buddy, you were sure he’d mention it. It was going to be a long night. 

The next morning, someone you didn’t recognize came in. “Good morning, can I help you?” 

She smiled softly. “Are you Y/N?” 

“I am.” You nodded. 

“I was told this is the best place to buy gifts. I’m driving through town and needed something for my family.” She motioned around. 

“Can I help you find anything in particular?” 

“Maybe something Doctor Who related and then some comic books?” She offered. “My son is into comic books lately.” She started looking around. 

Nodding, you went to help her find something for her son. “Does he like something specific?” 

She thought about it. “I don’t remember if he said he needed the next Marvel or Marvel X-men.” She pulled out her phone. “Let me call.” 

“Of course.” You nodded. 

She walked around the aisle. “Hey, Dean. Can you ask Ben again which comics he wanted?” She asked, not noticing you stiffen for a moment. 

So, this was who Jess saw? You chewed on your lip harshly as you busied yourself with stacking some books. You hoped that he mentioned it on your date that night, then you worried he’d cancel. He had to tell you. Knowing she went to your store, he had to figure you’d know. Your mind was racing all over the place.

“So, he asked for both.” She came over with a chuckle. 

“Alright, let me find those for you.” You went to focus on that. Once she gathered everything she wanted, you set it aside. 

She smiled gratefully. “Thank you.” She said sincerely. 

“You’re welcome.” You told her while looking for what she needed. 

Soon she had bags in hand. “I’ll definitely come by the next time I’m around.” She grinned. “Maybe bring my son next time.”

“Always happy to help.” You smiled. “Nice to meet you…”

“Lisa.” She grinned. “I’ve heard a lot about you.” 

“Oh?” You warmed. “Hopefully good things.” You didn’t want to tell her you had no idea who she was. 

“Of course. Dean said you were the sweetest person he’s ever met.” She chuckled. “And really easy to talk to.” She held out her hand. “I’m assuming Dean mentioned nothing about me.”

You blushed. “You’d be right.” 

She laughed. “Used to that.” She shook her head. “Old friend.” She explained. “Figured I’d stop in to say hi.”

She seemed so nice and you wondered why Dean wouldn’t mention her. “It’s nice to meet you. I’ve only met his family so far, so it’s nice to meet a friend of his.” 

She nodded. “I drive through about twice a year, maybe next time we can catch up? Dean’s being stingy.” 

“Stingy?” You tilted your head. 

“Doesn’t want to share his new girl with me.” She shrugged with a chuckle. 

“Oh.” You chuckled. “I’m mainly here so he may not have thought we’d have time.” You explained. 

“Maybe.” She agreed. “Well, thanks again. See you next time.” She waved. 

“Bye.” You waved back. “Ugh.” You sighed as she left. At least now you had answers. Now would Dean tell you? That’s the one question that was left. You just hoped he did. 

Dean had take out bags in his hands when he came in later. “Hey, babe.” He grinned.

“Hi.” You had set up a table for the two of you. “Let me get our drinks out of the little cooler.” You went to do that while he unpacked. “How was your day?” You asked as you came back.

“Good. Had a busy morning.” He sat. “You met Lisa?” He asked. 

You hid your surprise that he brought her up. “Yeah, I helped her find a couple things.” 

“Cool.” He nodded. “I also brought us dessert.” He showed you a container. 

“Thank you.” You smiled softly. “I’ve been looking forward to this all day.” 

“So have I.” He grinned. “Love our dates.” He went to kiss your cheek before sitting down. “Was it busy today?” He asked, wanting to hear about your day.

“Decent.” You nodded, watching him for a moment. “How was your day?”

“Had Lisa’s son for the morning then they left around noon. Caught up on work after that.” He explained. “Pretty easy day.” 

“She mentioned she was an old friend.” You tried. “That you’d told her a lot about me?” 

“Course. Told her how happy I am to be dating you.” He grinned. “About how great you are.” 

You blushed. “Dean…” You said softly.

“It’s true.” He chuckled. “And I promise I didn’t do it in the way that I was rubbing it in that I have a new girl to her. I’m not like that.” 

“A new girl? Why would your friend feel that way?” You tilted your head. 

“She’s my ex-girlfriend.” He shrugged. “I didn’t tell you?” 

You shook your head. “You didn’t mention her at all.” You told him honestly. “I didn’t know she existed until she came in the store.” 

“Oh. Yeah, we used to date.” He nodded. “Sorry.” He said it casually. 

“Oh, she didn’t mention that.” 

“She probably thought you knew.” He admitted. He shrugged a shoulder. “That’s all.” 

You nodded, glancing down. “She said she wanted to ‘catch up’ with me.”  

“She’s super chill. I think you’d get along with her.” He nodded. “Want me to give her your number so you can text before she comes back through?” 

“Uh…” You thought about it. “Wouldn’t that be weird for you?” 

“Nah.” He assured. “It’s been years since we dated.” He told you. “This was pre-Ben.” 

“How old is he?” You asked. 

“Twelve.” He shrugged. “So a long time ago.” It was another lifetime to him.

“Oh. That is a while.” You agreed. “It’s rare for people to remain friends after breaking up.” You mused. “So, that’s kinda cool.”

He grinned. “Yeah.” He nodded. “Only see her once in a while.” He explained. “Since we live a bit apart, and she’s doing the mom thing.” 

“Makes sense.” You chewed, glad you were talking about it. It took a weight off your shoulders. 

He looked up suddenly. “You weren’t worried, right?” He asked, just realizing that could have been a factor. 

You blushed. “Well…I was more worried that you didn’t tell me.” You admitted. You wouldn’t lie about that. “Then you seemed upset that Jess mentioned it so it felt like you were being defensive.” You went on, your voice gentle.

He watched you as you spoke. “Either way, don’t worry. Just friends.” He told you, hoping that reassured you. 

“I believe you.” You promised. 

He smiled at that, relieved. “Great.” He was glad this wasn’t something that would get between the two of you. He hadn’t really thought that it would until right then. “I’m sorry I didn’t tell you about her yesterday.” 

“It’s okay.” You said softly. “But thank you.” You did appreciate that. 

“I really did rave about you.” He told you. He chuckled as your blush deepened. “The whole time.” He winked. 

“You didn’t have to.” You assured. 

“Wanted to. My girlfriend is awesome.” He flirted. He was happy to make you smile. He loved your smile. You lit up a room. “Can we get a new picture together after?” 

You nodded. “Of course.” You agreed happily. You loved taking pictures together. One of your first pictures together was your phone wallpaper. 

He beamed. He could see you together for a while. He’d do everything he could to make sure that happened. He’d never felt this way before. It was so new, and he shockingly wasn’t scared. You were different. 

You kissed him softly when it was time for him to leave. He smiled against your lips. “See ya, babe.” He kept his arm around your waist. “Sleepover soon?” He winked. 

“I’d like that.” You hugged him. “This weekend? We can have a movie marathon.” You suggested, smiling. 

“Perfect.” He kissed your forehead. “I’ll text you later.” He promised. 

“Okay. Have fun.” You squeezed him. You waved as he left and smiled to yourself as you went back inside. You felt so much better after that lunch. It relieved you. You went back to work much happier. 

Sam came into the shop around Valentine’s Day. Dean hadn’t mentioned he was coming, so it had been a pleasant surprise. You hugged him and grinned. “I didn’t know you were coming!”

“Wanted to surprise you. And Jess.” He chuckled. “How’ve you been?” 

“Great!” You smiled. “Same old.” 

“Yeah? Still with my brother?” He smiled. 

You were confused how he wouldn’t know. “I am.”  

“Sometimes Dean exaggerates.” He explained, looking through your gift section. 

“How would he exaggerate us being together still?”

“Say you’re doing great but you’re not.” He shrugged. “That’s all.” 

You pouted slightly. “We’re doing great in my opinion.” You said honestly. “Even after I met Lisa.”

“Oh, you met Lisa?” He looked over. “I didn’t know that.” He looked so surprised. 

“Yeah, she stopped by not long after New Years.” You explained. 

“Did you meet Ben? Did you freak out like I did?” He came over, trying to slow the questions down. 

You raised an eyebrow. “No, Lisa came alone to get a couple things for Ben. Why would I freak out?” 

“Uh, no reason.” He shrugged. 

“Sam…” His tone led you to believe that was a lie.

He groaned. “Ben looks like Dean.” He said quickly. “But Lisa assured him that he’s not his.” He added. “So, yeah.” 

“Oh.” You blinked, unsure how to feel about that. “If she says he’s not his, he’s not his, right?” 

Sam shrugged. “You wouldn’t believe how much he not only looks, but acts like Dean.” He sighed. “So, I can’t say.” 

You stared at him. “Well, did Dean get a test?” You wondered.

“He took her word for it.” He explained. 

“Wow.” You breathed. How did you take this? If Dean didn’t press, then there was nothing for you to worry about. You trusted him. Or did he not press because he didn’t want kids? 

“I didn’t mean to cause any worries.” Sam saw your face. “I thought you knew.” 

You shook your head, sighing. “No.” You explained what had happened with Jess calling and everything after. 

He listened intently, wanting to help. He was a bit surprised that Dean seemed to really like you, but hadn’t mentioned Lisa. He was a bit upset at him for that. He’d have to say something. “Well, at least Lisa was nice.” He noted. That was something. 

“Yeah, she wants to ‘catch up’ next time she’s here.” You shrugged. 

“Might be fun.” He shrugged back. “Never know.”

“Hey, Sammy.” Dean grinned as he opened the door. 

“Hey, Dean.” He came in with his duffle. “Just came from seeing Y/N.” 

“Nice. Bet she loved that surprise.” He smiled. 

He set his things down. “Mostly.” 

“Mostly?” Dean went to get him a drink. “What happened?” He asked, confused. 

Sam looked disappointed. “Why didn’t you tell her about Lisa?” He crossed his arms over his chest. “Or that we all think Ben is yours?” 

Dean groaned. “Sam, please tell me you didn’t tell her you think that. Please.” He pleaded. Sam shrugged, making Dean groan louder. “Dude!” He threw his hands up. 

“What? You’re the one not telling her in the first place!” He countered. “You wouldn’t have to worry if you were honest.” 

“And have her worried? No.” Dean scoffed. “Now she’s probably wondering if Ben actually is mine!” 

“Aren’t we all?” Sam shrugged. “You’re the one who didn’t ask for a test.” This was an old argument. “Maybe now you finally will.” 

Dean glared. “This is old news.” 

“Not to her. And then you didn’t even tell her Lisa was coming. Jess had to warn her!” He shot him a look. “I know for a fact you didn’t tell her on purpose.” He shook his head. “You claim to really like her, but it’s like you’re sabotaging this on purpose.”

“No. I’m making sure that this relationship doesn’t get derailed because of an ex.” He fought. 

“So, why lie?” He asked. “It’s been over a decade since you were with her. You sent Lisa to her store . And what? Didn’t think Lisa would say something?” He scoffed. “C’mon Dean.” He tried. “You’re not being a good boyfriend if you’re lying.” He hoped that got through to him. “You’ll lose if you’re not honest.” 

“Well, it’s too late now. Now she’s probably worried.” Dean sat. He sagged. “I can’t imagine what she’s thinking.” He literally had no idea and he knew you probably wouldn’t tell him unless he asked. You hadn’t even mentioned Jess telling you about Lisa at first. 

“Look, I like her for you, I do. But I don’t know if you’re meant to work out.” Sam said honestly. “Not with what I’ve seen from you.” 

Dean glared. “And you’re the expert?” He snapped.

“I’m no expert but at least I don’t lie to my girlfriend.” Sam said simply. “Especially about something so big.” 

Dean shook his head. “I’ll fix it.” He promised. 

You were surprised when you were just about to close and Dean came in. “Oh, hi. Wasn’t expecting you.” You noted. “I was just getting ready to close up. Did you need to grab something?” 

He shook his head. “Want to go have dinner?” He asked, hopeful. “My treat.”

“Sure.” You smiled. “Just give me a few minutes to close up?” 

He nodded and tried to rehearse what he was going to say. He didn’t want to fumble his words. When you were locked up, he held your hand on the way to the diner. “How was work?” 

“Fine. I’m really glad Sam stopped by.” You smiled. “I know Jess will be excited to see him.” 

“Super excited.” He agreed. “Speaking of Sam…I know he mentioned the whole Ben thing.” He started as you reached the diner. 

“Yeah…” You nodded. “I was surprised.” You glanced at him. 

“Yeah, I know. To be honest, I didn’t want you to find out and worry.” He admitted. 

You nodded slightly. “I would have preferred you be the one to tell me.” 

“I blame Sam for that one.” 

“Would you just never have told me if he hadn’t?” That actually hurt. 

He glanced down. “I didn’t want you to worry about it.” He repeated himself. 

“You’d rather keep things from me so I don’t ‘worry’, instead of being honest and working through things?” You stopped in the middle of the sidewalk to look at him. That was a huge issue. 

“Well, I sound like a dick when you put it like that.” He sighed. 

“I really like you, and I know that I’m ‘shy’ and ‘quiet’, and all that…but I don’t want you to think I’m okay with you keeping things from me for any reason.” You said seriously. “That’s not grounds for a good relationship.” You pointed out. “And I won’t stay quiet about issues, especially something this big.” You said, tone firm.

He nodded. “I understand. I’m sorry.” He apologized. “I really am.” He said sincerely. “I’m not great at being a boyfriend and I’d hate to think I was the cause of it not working out.” He looked down. “I really really like you, and I really like being your boyfriend.” He let out a breath. “I’m sorry again.” He looked at you, hoping you believed him.

You sighed. “No more hiding things.” You urged him.

“Pinky swear. Cross my heart.” He nodded. He even held up his pinky for you. “And…would it make you feel better if I did that test for Ben?” 

You thought about it and nodded. “Why didn’t you do one already?” You asked, curious. “If he looks, and acts, like you?” 

“Why would Lisa lie?” He shrugged. “I’ve never had a reason to not trust her.” He explained. “I trusted her that she’d tell me.” He told you. 

“Okay.” You let out a breath. “If you don’t feel comfortable doing one, I won’t make you.” You didn’t want him feeling forced into anything. 

“No, if that’s what helps us, I’m all for it.” He said gently. “I’ll call her and talk to her about it.” 

“I hope it doesn’t cause issues.” You told him. “You two seem to have a good friendship.” 

“Nah, it’ll be fine.” He assured. “Do you still want to do dinner? Or would you rather not?” 

“Let’s do dinner.” Your tone was soft. “Did Sam go to see Jess?” You asked. 

He nodded. “Yeah, he was excited to see her.” He led you back down the sidewalk. He felt this was good for the two of you, that you’d had that talk. He knew he’d try and be more open and honest now. If he wasn’t, he’d lose you.

Dean called Lisa the next day, nervous. “Hey, Dean.” She answered. “What’s going on?” She asked, sounding a bit worried. He normally didn’t call her. 

“We need to talk.” He tugged at his hair and set his shoulders. 

“About?” 

“I would like a test done.” He blurted out. “For me being Ben’s dad.”

She stayed quiet. “Oh. But I told you…” She started.

“I know. And this has nothing to do with me not trusting your word, but I just need the test done.” He said gently. “I’ll pay for everything.” 

She sighed. “Alright. I’ll get that done soon.” She promised. “Can I ask why you suddenly want it?”

“I think it’s just best that I’m completely honest with Y/N right now.” He explained. “And I wouldn’t be able to tell her if I knew for sure or not.” He went on. 

“I’m not going to lie, I wasn’t sure what to expect, but that wasn’t it.” Her voice was filled with surprise. 

He couldn’t help but let out a half chuckle. “I’m sure it wasn’t.” He told her. “But, I really want things to work with her.” 

“Sounds like it. Well, if this helps…I’ll get it done soon.” She assured him. 

“Thanks. Appreciate it. Let me know what you need from me.” He sounded relieved. He had been worried she’d be upset. That she’d be mad he didn’t believe her. 

After they hung up, he texted you. Hi babe. Just an update on the test. She’ll do it soon. He sent. I’ll keep you updated.

Thank you <3 

He smiled, feeling hopeful this meant he was on the right track with you. Then he paused, a tiny part of him wondering what would happen if Ben was his. He paled a little. Would you leave him? What would he do? He’d have missed all these years with him. Would Ben hate him? They’d always gotten along! He groaned, unsure of how he wanted the results to go. He let his head fall back before texting you again. I don’t believe he’s mine, but if these results show he is…please don’t leave me?

You could practically hear the worry in his voice as you read the text. I wouldn’t do that. You promised him. I promise. Okay?

Thank you, sweetheart. You knew he needed that. You were just glad he wasn’t upset. That would have sucked. You wondered how long this test would take. It wasn’t like you had experiences with this. 

Dean rubbed his face as Lisa texted him that she hadn’t received anything yet. It felt like it had been ages at this point, even if it had only been a few months. He was surprised when moments later, he got a text from you. 

Dean… 

He instantly worried. Had he forgotten something? Was it your birthday? What’s wrong? He pushed all thoughts of Lisa from his mind. 

Uh, I’m *late*. 

He frowned. To work? He blinked. You were always early to work, you loved that store. 

Not the kind of late I’m talking about. 

It took him a minute and he rubbed his face again. “Shit.” He groaned. Could it be something else? 

I don’t think so. Usually I’m pretty on time. You sent back quickly. I plan to test tomorrow morning, but I wanted to give you a warning. 

Want me to be there? He asked. I can bring dinner tonight, sleep over, and then be there in the morning? 

Alright, if you’re sure. Have you heard from Lisa? You asked. 

She actually texted me right before you did. She hasn’t heard anything yet. 

Wow, it’s taking a while. I’m sorry to add to it. 

You did feel bad, and half wondered if you shouldn’t have said anything. Then you remembered you’d had him promise to be honest. It would be unfair if you weren’t. Sighing, you knew you’d be picking up tests after work. That wasn’t something you’d ever had to buy before. Word would get around quickly. Do you mind if I order them on Amazon or something? So no one is spreading rumors here? You asked him.

No of course not, I completely get that. He agreed. I’m off today, so I can always drive a town over, too? Whatever you think would be easiest, babe. 

You chewed on your lip in thought. I’ll order them. Come spend time at the shop if you’d like. You felt you both could use that. You could feel his worry and he probably could feel yours. I’ll send you some money for coffee :) 

Be there soon 😘

You looked up and smiled when you saw Dean. He rushed over to peck your lips. “Hey, babe.” He said softly. He knew you were probably really worried. He was. What if he got news that he was a parent twice? Neither of you had even mentioned if you wanted kids. Now didn’t seem like the time to ask. “Need any help with anything?” 

You shook your head. “Luckily it’s been a steady day, not too many crowds at once.” You sipped your coffee that he handed you. “So, just keep me company?”

He nodded. “I’ll set up a board game? Or do you want cards?” He asked, hoping that the two of you could have a relaxing day. Distracting, too. 

“Board game sounds good.” You smiled, happy he was there with you. “And the tests will be here in a few days.” 

“Alright.” He kissed your temple, pushing that from his mind. He hoped he heard from Lisa soon. Then pushed that away as well. He wanted to focus on spending time with you. 

The morning after the tests arrived, you slipped out of bed. You glanced at Dean who was still sleeping before making your way to the bathroom. You were so nervous as you set them up and a timer. What would happen if you were pregnant? You were so careful, and on birth control. You teared up, you were so scared. You sat on the tub and let your head hang as you waited. Your hands were shaking. 

Dean shuffled in as the timer went off. “Sweetheart?” He asked, moving a bit quicker when he heard you sniff. He assumed that you’d seen a positive test. He wrapped his arms around you. “I don’t know much about being a dad, but I’lol be the best dad I can.” He promised.  

You sniffed more. “You’re so sweet. I haven’t seen them.” You leaned your head on his shoulder. “Too scared.” 

He felt you shaking and held you tight. “I’m here. No matter what you decide to do or what the outcome is.” He rubbed your back. He was scared, too, but didn’t want to make what you felt worse. And he’d started trying to prepare himself to be a dad. Part of him thought it wasn’t the worst idea. You’d be a great mom no matter what. “Want me to look?” He offered. When you nodded, he worriedly looked to the sink. He took a deep breath and reached for a test. 

You shut your eyes tightly. How did teenagers go through this? You remembered a girl in your class getting pregnant at the end of your junior year. 

He looked at the tests before kissing your forehead. “You’re okay.” He breathed. “It’s negative, sweetheart.” 

You gasped and hugged him tightly. You were so relieved. 

He held you just as tightly. He could feel you relax, the tension in your body fading. He rocked you a little, kissing your head over and over. “Do you work today, babe?” 

You nodded, wiping your eyes. “I should get ready.” You let out a breath. 

He softly kissed you. “I’ll make you a quick breakfast.” He told you. “I’m off, want me to stop by for lunch?”

“Please.” You looked up at him tearfully. “Thank you for being so supportive.” You smiled. “I was scared this would push you away.”

He shook his head. “I wouldn’t leave you for something like this.” He hated that you thought that. “I never want you to be scared to come to me about anything.” He wiped under your eyes. “We’re a team now.” He kissed your forehead. “I know we’re always careful, but if we ever have to be sitting in here looking at a test again… please don’t worry about me leaving. I won’t.” 

You sniffled and nodded. “Okay, I’ll try. Thank you.” You were thankful he was being so sweet. It made your heart flutter. “You’re amazing.” 

“That’s you, babe.” He pecked your lips again. “Now I‘ll go make breakfast while you get ready for work, then I'll drive you and we can stop for coffee.”

“Thank you again.” You went to get your clothes once you tossed the tests away. Now you wouldn’t have that worry hanging over your head. That was a big one. 

You were texting with Jess later that day while it was slow, telling her about what had happened. 

If you don’t get your period in a few days, I’d see the doctor for a blood test to make sure it’s not a false negative. 

How often does that happen??? 

It took her a moment to reply. I googled it. About 48% of the time…

The panic hit you all over again. Jesus! What were you going to tell Dean? You didn’t want him to think you were overreacting. Should you just make an appointment for the following week in case? You decided to do that, just so you could be sure. And Dean still hadn’t heard from Lisa. You didn’t want to put more on his shoulders. Can you come with me if Dean’s not able to? You asked, not wanting to be alone for that. 

Of course! I’ll send you my schedule. <3 

Thank you <3 You paced a little bit. You thought you had been in the clear. You didn’t know that false negatives were so common. You’d have to tell Dean for dinner that night. That wasn’t something you were looking forward to. 

Dean could tell you were nervous at dinner that night. “Is everything okay?” He asked, offering his hand to you. “Did you have a dick customer?”

You pulled up your chat with Jess and got to the beginning to show him. 

He read it quietly and you could tell when the tension washed over him a bit. But he relaxed before looking at you. “Let me know when the appointment is, please.” He handed the phone back. “I’ll be there.” 

“Are you upset?” You asked worriedly. You were chewing on your lip pretty harshly. 

“No.” He said instantly. “I’m not upset.” He said truthfully. “When you first texted me I started preparing myself if I was gonna be a dad.” He shrugged. 

You glanced down. “I don’t know if I’m ready.” You were scared all over again. “And we haven’t even been together for 6 months.” 

He nodded. “I totally get why you’re worried.” He assured you. “Whatever you decide to do if it comes to be that were expecting.” He wouldn’t force you into anything. He’d support your choice. 

“Thank you.” You held his hand. “I’m sorry this adds to the weight on your shoulders.” You felt that wasn’t fair to him. “I think I’ll start researching everything tonight.” 

“Researching?” He asked. 

You nodded. “All our options. I don’t think I’ll be able to sleep, so that may help. I like being informed.” 

“Alright. Send me anything you want.” He sipped his drink. “I’ll read over anything you find interesting.” 

“You’ve been really sweet.” You smiled. “Thank you.” You breathed. 

“Of course, babe.” He smiled back at you. 

The next week flew by, and it was the morning of your appointment. Your hands were clammy and you couldn’t stop your leg from bouncing. Dean reached over to take your hand to comfort you. He kissed your knuckles once you were in the waiting room. He hoped that things went well. He had no idea what to hope for. He found himself going back and forth on it. 

Soon, you were called back. You didn’t focus on anything but your breathing. “Will the results be instant?” You asked. “Or will we have to wait?” 

“We’re doing both a urine sample, and a blood. One will be instant, the other days a few days.”

So you’d be worried for a few days still. “Alright, thank you.” You did everything they asked you to. Finally, you were sitting in the room just waiting for them to tell you the results of the first test. Dean kissed your temple gently. 

“Want to play tick tac toe on my phone while we wait?” He asked. When you nodded, the both of you focused on that. 

Soon the nurse walked in with your results. You held your breath. “Your urine sample was negative, but the blood sample takes time.” She explained. 

“Okay. Thank you.” You nodded, standing with Dean. Once you were back in his car, you let out a breath. “I don’t even know what I’m hoping for.” You told him honestly. “Just for this to be over with but there's so much waiting.” You glanced at him. 

He nodded. “I get that.” He agreed. “But at least with a blood test we’ll really know, right?” 

“Yeah, it’s pretty for sure.” You played with your hands. “Hopefully we know before the weekend.” 

“Hopefully.” He agreed. “Uh, Lisa texted me while I was in there. Want to be with me while I call her back?” He asked. “I can put it on speaker?”

You felt you knew the answer if she couldn’t say it over text. “If you’d like me to be.” 

He nodded and parked at your place before calling. “Hey, it’s me.” He winced. “Obviously.” 

“Hey, I got the letter and I didn’t want to open it without you on the phone.” She explained. “I felt that was the best way to do it.” 

“I get it.” He waited as he could hear her open the envelope. His heart was hammering in his chest.

You looked down as Lisa cursed. Swallowing, you knew. “H-he’s yours.”

Dean shut his eyes. “Dammit, Lisa. It’s been years.” He sagged. “I missed so much. Will he hate me?” 

“No. We will figure out how to tell him.” She promised. “And make sure he knows that this wasn’t you avoiding fatherhood.” 

He sighed. “Why didn’t you want the test in the first place?” He asked, sounding upset. 

She stayed quiet. “At the time…it was just easier. I didn’t really want us together anymore.” She said truthfully. 

You winced. That was harsh, and wrong. “So I missed out on being a father for years because you didn’t want a relationship? I could have easily been a dad without that. He’s nearly a teenager.” He argued. 

“I didn’t think you’d be around either way, Dean. I’m sorry, but it’s true. You were traveling all the time with your dad. You barely stayed long enough for us to work. I didn’t want to set myself up or my son for heartbreak.” She said firmly. “We would have been perfectly fine had we never done this test. You living in that town is the longest I’ve ever seen you stay in one place.”

Dean pinched the bridge of his nose. “You should have let me make that decision.” The two were getting heated. 

“I actually think it’s fine if we continue on the way we have been.” She decided. 

“Y-you’re not going to let me be a dad?” His heart sank. 

She stayed quiet. “I’ll think about it.” She said after a moment. 

You felt for him, and reached over to rub his back. 

“I hope you decide not to take this chance away from me. Again.” He hung up. He clenched his jaw. “I can’t believe her.” 

“I’m so sorry.” You said sadly. What else could you say? He’d missed so much of his son’s life, and might miss more. 

He leaned over and kissed your cheek gently. “Thank you for being here for me.” He rested his forehead on your shoulder. “And keeping me in the loop with everything that’s going on.” He couldn’t imagine finding out that Ben is his, and then finding out you’d kept this from him. 

“Of course.” You whispered. “I’ll always be honest with you.”  

“I appreciate that.” He squeezed your leg. “I need a bit of time to process this. But I’ll be by for dinner?” He asked. 

“Take your time.” You told him. “Just text me if you decide to stay home?” 

He nodded and hugged you the best he could. “I’m just not the best person to be around when I’m upset.” He admitted. “I don’t need you seeing that.” 

“I want to help, though.” You pecked his cheek. “So come over whenever you feel.” You said softly before getting out of the car.

He waved. “I’ll text you.” He promised. 

You laid in bed that night, staring at the ceiling. You put your hand on your stomach. You had no idea what the future held but at least you knew you’d let Dean be in their life. You couldn’t imagine keeping his baby from him. The thought hurt your heart. He deserved the opportunity. It wasn’t like he was some horrible man that shouldn’t be around kids. He was an amazing guy. You wondered if his relationship with Lisa was making her biased. It sounded like he wasn’t around a lot. Letting out a sigh, you rolled to your side. Your mind was all over. Now you were truly confused as to what you wanted to hear when you got that call. You wondered what Dean was hoping for. 

Dean was sitting in his living room, whiskey in hand. His head was hanging as he already had a few. He didn’t think Lisa had thought that badly of him. Did she think he’d be a shit dad? What were you thinking now? Now you were probably hoping it was negative. More so than you already were. And now he found himself wanting the opposite. A chance. He possibly had a chance. But he didn’t want to force that on you. He was thankful that at least you promised not to do what she had done. He knocked back his drink and poured another. He glanced over when he saw Sam calling. “Sammy!” He mumbled as he answered. 

“Are you drunk?!” He asked instantly. 

“Dude. All I said was your name.” He huffed. “But yeah. Maybe.” He let his head fall back. “Ben’s mine.” He muttered. 

Sam stayed quiet. “Shit.” He breathed after a moment. “How do you feel? How did Lisa feel? Y/N?” He asked. 

Dean scoffed. “Lisa doesn’t wanna let me be a dad.” He told him about their conversation.

She stayed quiet. “At the time…it was just easier. I didn’t really want us together anymore.” She said truthfully. 

You winced. That was harsh, and wrong. “So I missed out on being a father for years because you didn’t want a relationship? I could have easily been a dad without that. He’s nearly a teenager.” He argued. 

“I didn’t think you’d be around either way, Dean. I’m sorry, but it’s true. You were traveling all the time with your dad. You barely stayed long enough for us to work. I didn’t want to set myself up or my son for heartbreak.” She said firmly. “We would have been perfectly fine had we never done this test. You living in that town is the longest I’ve ever seen you stay in one place.”

Dean pinched the bridge of his nose. “You should have let me make that decision.” The two were getting heated. 

“I actually think it’s fine if we continue on the way we have been.” She decided. 

“Y-you’re not going to let me be a dad?” His heart sank. 

She stayed quiet. “I’ll think about it.” She said after a moment. 

“Well, that was harsh of her.” Sam defended him. “And complete bullshit.” 

“I agree! At least Y/N said she’ll let me be there.” He sighed. “If she is…I assume Jess told you.” He rambled. 

Sam was quiet for a moment. “Wait, what? What’re you talking about?” 

Dean groaned. “We’re in the middle of a pregnancy scare.” He told him. “She took a couple at home tests, and they were negative, but still…no period. So, she went to get blood work this morning. We’re waiting for that to come back.” 

Sam made a noise. “Dean…” 

“I know.” He sighed. “It was right after that appointment that I found out Ben’s mine.” 

“No wonder…” Sam sighed. “That explains you being drunk.” 

“Yeah.” Dean agreed. 

“Well, hopefully you guys find out soon.” He said gently. 

“Few days at least.” He sighed. “We’re hoping for it before the weekend.” 

“I’ll hope for you.” Sam told him. “Let me know when you find out?” 

“Course. Probably the first one we tell. Well you and your girl.” He added. “I’m sure she’s been texting Jess today after I dropped her back off.” 

“Probably.” He agreed. “Let her know you have my support. Always.” He liked you, you were someone he saw as a friend. 

“Thanks, man. I’m sure that’ll mean a lot. She’s scared.” He sighed. 

“Yeah, I could imagine. Are you?” He asked. “I would be.” 

“Scared shitless.” He admitted. “But is it bad part of me isn’t?”

“Mm. I don’t know. Never thought you’d be the family type.” He said honestly. “I figured that was the last thing that you’d ever want.” 

He sighed. “Maybe at one time. But she’s different.” He admitted, sipping his drink. 

“You may not have a choice.” Sam noted. “And you have to accept that.” 

“Yeah, I will.” He sighed. “I’ll call you if I hear anything.” He promised. 

“Great, bye Dean.” Sam hung up. 

Dean glared at the door when someone knocked right before he was about to fall asleep. “Damn it.” He muttered, getting up to get the door. He stumbled as he opened it. “Sweetheart?” He frowned. “What’s wrong? Couldn’t sleep?” He let you in.

You shook your head. “A-are you drunk?” You asked gently. 

“Yeah.” He winced. He rubbed the back of his neck. 

“Want me to get you some water? And I can leave?” 

“If you want to leave, but you can stay.” He went to clean up. He didn’t know if him being drunk was making you uncomfortable. 

You gently pushed him onto the couch so he could sit before you cleaned up. You wanted to help him however you could. You brought him some water before sitting next to him. You kissed his shoulder before putting your head on it. 

He held your hand. “What if Lisa didn’t tell me because she really felt I’d be a bad dad?” He slurred. “And what if she’s right?”  

You felt for him. “She’s not right.” You assured him. “You’re amazing, and I think you’d be a great dad. Fun, and caring.” You said firmly. “I really think that.” You gave his hand a small squeeze.

He sniffled after a bit. 

Hearing him like that hurt. You moved so that you could hug him. “Let’s get you into bed, okay? So you can sleep this off.” 

“Stay?” He asked. “Please?” 

“Of course.” You could tell he needed you there. You’d cuddle him up. Getting up, you tugged him up so that you could help him to his room. He stumbled on your side. You knew he was probably really hurting. You helped him change into sweats. Once he was in bed, you changed into one of his shirts and crawled into bed next to him. He held you close and kissed your shoulder. 

“Thank you for coming.” He mumbled. “You’re amazing.” He muttered as his eyes got heavy. “M’lucky.” He soon started to softly snore. 

You let out a soft sigh and closed your eyes. You had no idea how to feel. At least you could comfort him. You hold him and make sure he woke up with you. 

Dean groaned as he woke up the next morning. He hated hangovers so much. He shifted, then realized he wasn’t alone. He opened one eye and relaxed when he recognized your hair. He couldn’t remember you coming over, but was glad you were there. He held you tighter and just relaxed. 

You felt Dean move and stretched a bit. You nuzzled to his chest and smiled. You hoped that he woke up doing better. 

“Babe?” He mumbled. 

“Yeah?” You yawned.

“Favor?” He asked. 

“What do you need?”

“Hangover food.” He groaned. “Something greasy?” 

You nodded. “I’ll go do that.” You agreed.

“You’re the best.” He sighed contently. “I owe you a huge date.” He told you. “I’ll plan something amazing. When my head isn’t pounding.” 

“It’s okay.” You smiled and went to find something for him. You brought him water and aspirin before starting to cook. You felt nice helping him. 

It didn’t take long for his apartment to start smelling good. He sat up eventually after the aspirin worked a bit. He shuffled out of his room to go to the kitchen. “Smells amazing, sweetheart.” He complimented, going to pour a mug of coffee that you’d brewed. “You’re the best girlfriend ever.” 

You blushed at that. “I don’t think me making you breakfast makes me the best.” 

“It really does.” He kissed your head. 

You plated up his breakfast and handed it to him. “If that’s what you believe, I won’t argue.” You smiled.

“I’ll remind you often.” He took a huge bite and nodded. “So good.” He sat and focused on his plate. “I feel better already.” He smiled at you as you brought over your own plate, sitting across from him. “Thank you.” 

“You’re welcome.” You beamed, happy to help. “Do you work today?” 

“No, thankfully.” He shook his head. “I don’t have to worry about a hangover at work.” 

“Good.” You smiled. “You can relax and get some rest.” 

“Do you have to go in right away?” He hoped you could stay a bit longer. 

“I should go in no later than 10, honestly. That’s pushing it.” You explained, glancing at the time. “But I'll text you when I can.” 

“Okay. I’ll go by as soon as I feel better.” He peomised 

“No rush.” You stood. “I better go and get ready.” You finished your juice and got up to bring your dishes to the sink. 

Dean watched you, falling harder for you. He grinned as you came over to kiss his cheek. “Thank you, babe.” He wrapped an arm around your legs. 

You chuckled and played with his hair a bit. “I’m glad I decided to come over. Or you would have slept alone.” 

He squeezed you. “That’s what I had planned on. Didn’t mean for you to see me like that.” He shook his head. 

“I’m with you, Dean. Good and bad.” You said gently.  

“Me too, sweetheart.” He promised. “Have a good day at work.” He said lovingly. gly. 

You kissed him once more before heading out to head home to get ready for work. 

I just got a call from my doctors. I have an appointment to talk about my blood test. Monday morning at 8am. You sent Dean.  

Okay, I’ll be there babe. He was so damn nervous.  Monday couldn’t get there fast enough. Sleepover Sunday night? 🥺 

Of course 😍 You replied quickly. I’ll make dinner. You added. Chicken parm? 

Perfect, sweetheart. 

The nurse came in and smiled softly. “I have your results.” She told you. 

Dean had his fingers laced with yours. “Alright.” You breathed. 

“You’re about 10 to 12  weeks pregnant.” She explained. “We’ll need to do a ultrasound to know for sure when your due date is.” 

Dean looked at you and saw you looked way more scared than he felt. “Thank you.” He said softly to the nurse. “Can we schedule that?”  

“Yes, we can get that set up.” She assured. “I’ll get that ready for you.” She left the two of you alone. 

“I’m sorry.” You managed.  

“Don’t be.” He kissed your knuckles. “Please.” He pulled you into a hug. “We’ll figure this out.” He promised. “And I’m not going anywhere.”  

You sniffled, feeling like you were forcing this onto not only him, but on yourself. “I’ll have to tell my dad.” Which was an obvious statement. 

“Mine, too.” He agreed. “Do you want me to go with you when you tell your dad?” 

You thought about it. “Not right away, but maybe we can set up a dinner?” You suggested. “Have him over to my apartment?” 

“Speaking of, do you want to find one together so we can both be there all the time for them?” He asked. “But yeah, we can make that dinner together.” 

You nodded after a moment. “Okay.” You looked over as the nurse came back in. 

“Your appointment is next Wednesday at 10:30.” She handed you a card. “And feel free to call us anytime.” She said gently, seeing how upset you were. 

“Thank you.” You took it and got up. Dean thanked her as well and followed you out. 

Dean helped set some boxes down. “Didn’t think you’d actually move out here.” He told his brother. 

Sam chuckled. “Well, Jess and I are getting pretty serious.”  

“Yeah, but…” Dean shrugged. “I get it.” He told him truthfully. “Y/N and I are trying to find a place.”  He looked at Sam. They hadn’t told a lot of people, just your dad but he needed to tell his brother. “She’s pregnant.” He told him. “She’s nearly 14 weeks now.”  

Sam paused. “Oh…” He breathed. “Wow, Dean.” He brought him in for a hug. “You know I’ll be here for you guys.” He promised. “Whatever you need.” 

“Thanks, man.” He sighed. “I can tell she’s scared.” He told him. “Only her dad knows so far. I don’t even know if she’s told Jess or Kevin.” 

“I’m sure she is. That’s huge. No wonder you’re moving in together. A baby is huge.” 

“A what?” John asked as he carried a box in. 

“Nothing.” Sam backtracked. 

John set the box down, looking at Dean. “Did I hear somethin’ about a baby ?” 

Dean sighed. “Yeah, you did.” He ran a hand through his hair. “Y/N is pregnant, and we’re looking for a place.” 

“You’re shitting me.” John stared at him. “Please tell me this is some dumbass joke.” 

“Why would I joke about that?” Dean shrugged. “And why’re you pissed?” He asked. 

“Because you two won’t last, and now you’re gonna put a poor kid through getting raised between two houses.” John shook his head. “It’s obvious you two won’t last. Even Sam knows that.” 

Sam put his hands up, not wanting to be in the middle. “Leave me out of this.” 

Dean looked at Sam, hurt. “You don’t think we’ll last?” 

“Not at the beginning.” Sam winced. “Jess didn’t either.” 

“Thank you.” John nodded. “You’re too different.” He stated. “Now she’s tied to you forever.” He shook his head. “No matter what she wants to do in life, she will always have to worry about what you want.” He pointed a finger at him. “You know better. The same thing happened with Lisa.” 

Sam winced, knowing that didn’t help whatsoever. 

Dean clenched his jaw. “I got lied to for years about Ben, how is that worrying about what I want? She kept my kid from me.” 

John shrugged. “She did what was best for her.”

“Dad.” Sam sighed. “Please stop. Give him some credit for wanting to be a dad. Some guys walk away without caring.” He mentioned. “Dean really wants to be there for them. That’s way better than making her be alone.” He defended his brother. “Even if they don’t work out in the long run, Y/N will always know that Dean will be there.” 

Dean crossed his arms. “And I happen to think we’ll work out great.” He added. “So I think we’ll last.”

“Your mother is going to be so damn disappointed.” John told Dean, knowing how much his son loved Mary. 

Dean glared a bit. “At least she’ll support me.” He snapped. 

“There are a lot of raised voices coming from up here.” Mary came in. “Why is it you boys can’t get along? What is it this time?” She sighed.  

John looked at Dean expectedly, making him sigh. “Y/N’s pregnant, Ma.” He told her. “She’s about 14 weeks along.”

Mary let out a breath. “I see.” She said calmly. 

“And dad’s being a dick about it.” Dean went on. Sam nodded in agreement easily. 

“Dean, don’t call your father a dick.” She told him. “John, why are you being like this towards Dean having a family?” 

“I told you they wouldn’t last.” John started again. “She’s gonna be stuck being a single mom, just like Lisa.” 

“That was Lisa’s choice. Y/N made her choice to want to keep me around. Which I’m grateful for.” Dean defended. “I want to be there for them, and I’m trying to be there for Ben, too.” 

“Why are you mad at that, John? He’s being supportive of both of them.” Mary asked. “I would think that would be something you want. For him to step up and be the best father he can.” She crossed her arms. “We can’t be upset with him.” She put her foot down on this matter. “We are grandparents, and I want to be there for my grandchildren.” 

John rolled his eyes but didn’t argue with her. He knew that wouldn’t end well at all. 

Mary turned to Dean. “Is she working right now?” She asked him, making him nod. “What’s her favorite coffee? I’ll bring her some and give her my support.”

“I think she’s cutting out coffee right now.” He told her. “But she likes that strawberries and creme frap thing.” 

“I would like to visit.” She smiled. “You boys behave while I’m gone.” She pointed to Dean and John. 

“You’re leaving me with them?” Sam nearly whined. “I get put in the middle of them.” 

“Come on.” She tugged his arm. “You can come with.” 

Dean huffed. “Wimp!” He shot Sam a look as they left. 

You were stocking some books when the doorbell rang letting you know someone was there. “I’ll be right with you!” 

Sam rushed over to help with the higher ones. 

You jumped. “Oh, hi!” You chuckled. “Thanks, saves me from using the stepstool.” 

“Yeah, not the first time I’ve gotten that.” He chuckled. 

“What brings you in today?” You asked. 

“To visit you.” He smiled. 

“And me.” Mary chuckled. She came over, handing you your drink. “Dean said you liked the strawberry frappe. I got extra whipped cream.” 

You gasped. “Thank you.” You hugged her. “I didn’t know you were in town.” You chuckled.

“Surprise.” She grinned. “We’re here helping Sam move into their new place.”

“That’s so great. I’m bringing sweets for your housewarming party.” You told Sam. “Homemade, too.” You grinned. 

“Appreciate it.” He smiled. 

“Listen…” Mary started. “Dean told us.” Her voice was soft. “About the baby.”

Your smile fell. “Oh. I’m so sorry.” You looked down, stirring your drink with the straw. 

“Sorry? Don’t be sorry.” She rubbed your back. “There’s nothing to be sorry for.” She assured you. “We’re here for you.” She promised. 

You glanced at her. “You’re not mad?”

“I can’t be mad.” She assured. “You are both adults, and are both good people.” 

Sam nodded. “A niece or nephew is cool.” He smiled. “And I’ll be around to help.” 

“Thank you.” You smiled softly at the both of them. “I really appreciate it. I’ll keep you updated.” You promised Mary.

“Maybe an ultrasound or two down the road?” She smiled. 

You nodded. “I’ll have Dean text you a copy of the first one.” 

“Thank you.” She beamed. “I’m excited.” She said honestly. “I’d like to be in their life no matter what.” 

“Of course.” Did she worry you’d keep the baby from them? Like Lisa maybe? You swallowed, hating that they’d think you were like that.

The two hung out for a bit at the store. It was about dinner time when they started to head out. 

“Hopefully we can have dinner before we leave.” Mary smiled. “Go out to eat somewhere nice.” 

“Sure.” You agreed, waving to them as they left. You locked the door behind them to go sit in the back to eat the dinner you’d packed. You wondered how John took it. You felt he didn’t like you, so probably not well. Sighing, you hoped to see Dean soon. You didn’t currently have any date plans. Dating had kind of been put on the back burner. You just hoped that it didn’t stay that way. That this would change everything. You pulled out your phone to text him. Date night soon, please? We haven’t had one since we found out about the baby. 

It took a moment since he was probably helping. Sure, babe. Whenever you’d like. He sent back before sending another. Want me to sleep over tonight? 

Please if you can. You needed that. 

I’ll be there around eight. He promised. Any cravings, babe?

You chuckled to yourself. He was so cute. Fruit. That’s about it :)  

I will bring fruit and cuddles. He promised. 

Yay! <3 

Dean held you close that night, wanting you to know he wanted to be there. He hated that he hadn’t taken you out on a date in a few weeks. “Did you have an area of town you wanted to live in?” He asked. 

“It’s all pretty nice, but maybe closer to the park?” You traced patterns on his chest. “There’s a couple of places in mind. They need a little work though.” You noted. 

“As long as it’s safe, I don’t mind putting in the work.” He said gently. “We can make it ours.” He said happily. “Get ready for the little one.” 

It warmed your heart to hear his excitement. “I don’t work the day after tomorrow, do you? We can look at them to see what you think.” 

“Nope, we can go.” He kissed your head. “And have a lunch date, too?” 

“Perfect.” You agreed. You rolled over to wrap your arm around him. “Thank you.” You said softly. “Does your dad hate me?” You asked suddenly. 

“Nah. Hates me though sometimes.” He admitted. “He’d never hate you.” He shrugged. “He was upset at me.” He explained what was said.

“A what?” John asked as he carried a box in. 

“Nothing.” Sam backtracked. 

John set the box down, looking at Dean. “Did I hear somethin’ about a baby?” 

Dean sighed. “Yeah, you did.” He ran a hand through his hair. “Y/N is pregnant, and we’re looking for a place.” 

“You’re shitting me.” John stared at him. “Please tell me this is some dumbass joke.” 

“Why would I joke about that?” Dean shrugged. “And why’re you pissed?” He asked. 

“Because you two won’t last, and now you’re gonna put a poor kid through getting raised between two houses.” John shook his head. “It’s obvious you two won’t last. Even Sam knows that.” 

Sam put his hands up, not wanting to be in the middle. “Leave me out of this.” 

Dean looked at Sam, hurt. “You don’t think we’ll last?” 

“Not at the beginning.” Sam winced. “Jess didn’t either.” 

“Thank you.” John nodded. “You’re too different.” He stated. “Now she’s tied to you forever.” He shook his head. “No matter what she wants to do in life, she will always have to worry about what you want.” He pointed a finger at him. “You know better. The same thing happened with Lisa.” 

“So basically no one thought we would last except us and my mom.” He sighed. 

You sagged at that. “That’s…not even my cousin.” You sighed. That really hurt if you were being honest. 

“Yeah, felt the same way hearing it from Sammy.” He sighed. 

You buried your face in his chest. 

He hugged you tight. “Screw them.” He rubbed your back. “We have us and our little family.” He said softly. “That’s what matters.”

“Thank you.” Your voice was muffled. Hearing him say that helped a lot. You could tell he supported you. You sniffed a bit.

“No, babe.” He said sadly. “Didn’t mean to make you cry.” He told you. “How can I help you cheer up?” He rubbed your side. “Back rub? Ice cream?” He tried. “Warm bubble bath?” He added. “I can look up dad jokes? Start practicing?” He hoped that the idea of him saying dad jokes would amuse you. 

“You’re gonna have the best dad jokes.” You just knew it. “You’re also the hottest dad.” 

He chuckled. “And you are the hottest mom.” He grinned, making you look at him. “The most beautiful.” He pecked your lips. “The most caring and sweetest.” He went on, his voice soft. 

You melted. “Thank you.” You breathed. “Needed that.” You kissed his jaw. 

He smiled as you did. He loved that feeling.

Dean had a few guys from the hardware store helping as he fixed the porch. You were at work, and he really wanted this done before you got home. This was the last thing on the list before painting. Then you both could move in. You’d finally be living together! And he was excited to start the nursery, and a room for Ben. It had taken a few months to get it all fixed up. 

Hearing a car, he turned to see you pulling into the driveway. He waved happily. “Hi, babe!” He went to greet you. “How’s our little one today?” You had a small bump. He loved it. 

“Good.” You kissed his cheek. “Just a couple days and we know what we’re having.” You reminded him. 

“Great.” He pecked your lips. “I’m so excited.” He said lovingly. “I think we’re having a girl.”

“Yeah?” You grinned. “What makes you say that?” You asked. 

“Just a feeling.” He nodded. “Is dad’s intuition a thing?”

You giggled. “Probably.” You nudged him. “You’re adorable.” You laced your fingers with his. “How’s the house coming?” 

“Almost done. Then I can paint tomorrow.” He nodded. “We should be able to move in in a few days.” 

“I’m all ready to go.” You grinned. “All packed up and everything.” 

He kissed your head. “So am I.” He couldn’t wait to wake up next to you every day. He was so excited and had put in a lot of work so far. “Want to sleep over at my place tonight?”

“Yes, please.” You hugged his middle. “I love our sleepovers.” 

“Soon that’s all we’ll have.” He said happily. “Dinners together all the time.” He noted. “Coffee! Midnight snacks!” He was clearly excited.

You kissed his jaw. “And less sleep in a few months.” You pointed out. “I can’t wait to see you with them.” You rubbed his chest. “You’ll be adorable.” You beamed. 

“I’m not now?” He grinned.

You pretended to think. “Well…” You mused. 

He tickled your side. He grinned as you laughed. 

“You’re adorable!” You promised. “And I’m lucky you’re mine.” 

“I’m the lucky one.” He sighed happily. “I have you, and we’re having a baby.” He rubbed your middle. “I can’t wait to feel them kick.”

You loved how excited he was. It had helped your worries a lot. If he was indifferent, or upset, you’d be in a different mindset. Thankfully, he was nothing but excited. “Almost done here for today? If so, want me to head to my place and make us lunch before I pack me a bag?” 

“Yes, please.” He agreed. “Just about done.” He said proudly. “I’ll text you when I’m on my way.” 

You kissed him softly before leaving to do that. You looked forward to having a sleepover that night. 

“Who do you want to tell about what we're having?” Dean asked. 

You thought for a moment. “I know I’d like to tell Kevin. He’s always been supportive. And your mom.” 

“She’d love that.” He grinned. “She thinks it’ll be a boy.” He smiled. “She’s so excited. She even started working more so she could take off some time when they come.” He told you.

“That’s so sweet!” You were happy she was being so supportive. 

Dean was glad the two of you seemed to get along. “And Lisa said Ben can come part of next summer.” 

“Hopefully that’ll be okay.” You nodded. “I haven’t met him, so I hope that he likes me.” 

“I’m sure he will. He’s just in that grumpy stage.” He explained. “Being a teenager and all that.” 

You smiled. “Can’t blame him for that. Maybe we’ll call your mom after we find out?” You asked, and you wondered if his dad was coming around. You hoped slightly. You didn’t want that lingering. That would suck. 

Mary beamed as you called. “How did everything go?” She asked instantly. 

“Great!” Dean said excitedly. “They’re doing okay.” He assured her. “We also found out what we’re having!”

“Can I know?” She gasped. “Or is it a secret?” 

He chuckled. “We’re having a…” He started. “Boy!”

She cheered. “Yay!” She chuckled. “A little you!” She was over the moon. “I can plan presents now.” She told him. “I’d there anything you think Y/N would like?” 

“She said something about fluffy slippers.” He mentioned. 

“Those I can find.” She assured. “She’ll want comfort after having him, and towards the end of pregnancy.” 

“Is there anything I can do?” He half whined. 

“Just be supportive but it sounds like you already are.” She smiled. “Maybe offer a foot rub, or get her one of those foot massage things.” 

“Okay, I’ll look.” He promised. “Thanks, ma.” 

“Of course. Let me know when your house is all done?” 

“Aside from the nursery and Ben's room, it pretty much is.” He said proudly. “We’re here full time.” He was grinning. “She’s been having fun decorating.” 

“Awe, how sweet.” She said happily. “Send me pictures later?” 

“Will do.” He agreed easily. “Talk soon?” 

“Of course.” She said her goodbyes and went to tell John. She was beaming. “We’re getting another grandson!”

“That’s nice.” He focused on the paper. 

“John Winchester. Do you have no intention of knowing our grandkids?!” She took the paper from him. 

He sighed. “Of course I do.” He looked at her. 

“So why are you acting like you don’t care?” She shook her head. “You haven’t spoken to Dean in weeks.” She crossed her arms over her chest. “I’m sure she thinks you don’t like her.” 

“Will they last? I meet her and in a few months Dean leaves?” He asked, annoying her further.  

“You’re impossible.” She muttered. “She’s still the mother of our grandson. She’s family.” 

“Yeah.” John said simply. 

She shook her head and walked away.  “That man.” She sighed. At least she would be welcoming to you.  With open arms. She decided to make you a little spa package. She’d bring it over soon. Even if John refused to go. 

Dean finished putting the lettering on the wall of the nursery. The two of you had finally named your son, and he wanted everything perfect for him. He would be coming any day now. You were relaxing more, and had even hired Sam for part time at the store. He knew his brother loved it. You had Jess and Sam over a couple times a month for dinner. He loved those nights. 

“How’s it coming in here?” You asked from the doorway. 

He looked over. “Just finished.” He grinned. “How’s our little guy today?” 

“Active.” You rubbed your belly. “I’m looking forward to holding him, but I’m not gonna lie…I’m gonna miss feeling him.” 

He grinned and rubbed your side. “I’m sure you will.” He kissed your cheek. “You’re amazing.” He said lovingly. 

“You’re more amazing. Going out for whatever I’m craving if we don’t have any.” You grinned. “Foot rubs…all that.” You wrapped your arms around him.

He kissed you softly. “That’s what I’m here for.” He promised. “Do you work this afternoon?”

You shook your head. “Not today. You?” You hoped you had all day with him.

“Nope.” He held you. “I’m all yours today.” 

“Lots of cuddles?” You smiled. “Movie marathon?”

“The Hobbit?” He asked, looking hopeful. You thought it was adorable. 

“Sounds nice babe.” You agreed. “I’ll make us some snacks.” You went to do that. You looked forward to cuddling up with him for the afternoon. It was what you both needed. Soon, it would be harder to do that. You both knew that. 

You rested while Mary made something for lunch. Dean was currently tucking in your son. He was a couple weeks old, and you still couldn’t believe he was here. You and Dean both cried when he came. You fell more in love with him the first time you saw him holding him. He was amazing. You were so glad you had him. You hoped to tell Dean you loved him soon. Despite having a baby together, neither had said it. You knew he was probably scared, as were you. But you really loved him, and wanted him to know that.  

Dean held you close as you both rested. He kissed your shoulder gently, glad that you were able to get some sleep. He didn’t realize he fell asleep until he was blinking awake again. He yawned, pouting that he was alone. 

You came in with a smile, holding two plates of food. “I just fed Nathan, burped him, now he’s in his swing while your mom watches him.” 

He let out a beam and let you settle next to him before turning your chin so you could look at him. “Sweetheart…” He breathed. He pecked your lips. “I love you.” He breathed. “So damn much.” 

You slowly grinned. “You do? I love you, too!”

He pecked your lips again. “Tell me again.” He asked. 

“I love you.” You told him. 

He smiled and kissed your cheek. “Thank you.” He couldn’t believe you loved him. “I was so nervous to tell you.”

You grinned. “That’s cute. Don’t be nervous, now.” You told him. “I was nervous to tell you, too. That’s why I hadn’t.” 

He kissed your forehead. “Well now we can just be one of those lovey couples who tell each other they love them all the time.” He said excitedly. 

You giggled, kissing his jaw. “Yes, we can. And Nathan will grow up surrounded by love.”

“Yes, he will.” He said happily. “Can’t wait to teach him everything.” He focused on eating for a minute. “Cars, especially. Oh no, what if he hates cars?” He blinked. 

“You’ll still love him and bond over something else.” You assured. “Way in the future.” You kissed his cheek. “For now, he’s just content with milk and naps.” You chuckled. “And cuddles.” 

“We’re great at that.” He grinned. “I love our life.” He said happily moments before he heard Nathan’s cries. “I got him.” He got up to go get the newborn.  “Hi, Nate.” He said softly. He cuddled him close. “Wanna go see mommy?” He asked softly. He brought him over to you and smiled. 

“Hi, handsome.” You smiled as you took him. “Nice nap?” You let him rest on your chest. 

Dean watched you lovingly. You were a great mom already. A natural. 

Jess helped set the table as you put Nate in his seat. “He’s so cute!” She gushed. 

You grinned at her. “Thanks.” You kissed the top of his head. “I’m glad he got Dean's eyes.”

She grinned. “That is adorable.”

“Let’s hope he doesn’t get my attitude.” Dean joked as he came in. 

“Oh, we can really hope.” Jess agreed with a chuckle. “Especially for Y/N.” 

You hugged Dean’s waist. “I love his attitude most of the time.” You kissed his cheek. 

Dean beamed and held you close. “I love yours all the time.” He said happily. 

Jess shook her head with a smile. “Saps.” She giggled. 

“Do you love my attitude?” Sam asked as he came in. 

“No.” Dean smirked. “No one does.” He teased. 

Jess scoffed. “Course I do!” She countered. 

Sam chuckled. “Good.” He grinned at his nephew. “He’s getting so big.” He loved being an uncle. He looked forward to watching Nate grow up. He was surprised at how quick the weeks had gone since he arrived. And how Dean was such a good dad so far. He could tell Dean loved his life. He hoped it kept up. That he didn’t get tired. 

Soon, they were all sitting and enjoying dinner. You had started to plan the holidays again. It would be your third with Dean.  And you were excited. You couldn’t wait to see how Nate reacted. You had been decorating like crazy. Dean had loved it. It reminded him of his own mom when he was a kid. He reminded you he loved you everyday. Soon, though, you were talking about how you needed to get back to work. But you didn’t know how to do that with Nate- daycare was expensive. You had no idea yet what to do. You wanted to help with bills, but it was looking like you couldn’t. Sure, you now owned the store, which helped… but you’d need Sam to be full time. And he couldn’t do that. 

You debated just having Nate at the store with you. It was your store now, after all.  But what if you couldn’t help someone? That worried you. Maybe you could hire someone to work at the same time as you? But did your shop do well enough for that? You’d have to look at your financial side of things. 

You were jerked from your thoughts as Nate let out a coo.  You looked at him instantly. You couldn’t help but smile. He was such a happy baby. You scooped him up and cuddled him. You listened to Sam talk about his classes. You were glad that he’d enjoyed college and law school. So did Dean as he always looked so proud. 

“Can I hold him for a bit?” Sam asked after a bit.

“Of course.” You went to him so he could get him. “He loves time with his uncle.” You set him in his arms. 

Sam beamed and Jess gave him heart eyes. She loved watching Sam with Nate. He was adorable. “Maybe me and Sam can babysit him soon so you and Dean can go one a date?”

“We’d love that.” Dean agreed. He appreciated her offering. “Thanks, guys.” He smiled. 

You fixed your scarf as you and Dean walked. You were on your first date since having Nate. You felt excitedly nervous. It was the first time you were away from your son. You had to have Jess reassure you. “Dinner first, babe?” Dean asked you.

“Sounds good. Hot cocoa after?” You smiled. 

“Perfect.” He winked. “And maybe once he’s asleep for his first couple hours tonight some not so family friendly cuddling?” He asked, hopeful. He missed you. 

You blushed. “I like the sound of that.” You said shyly, missing him too. You gave his hand a squeeze. The two of you walked to dinner and it felt like old times. Jess would randomly send you pictures, too, which helped. 

While you had hot chocolate, Dean handed you a box. You looked at him, curious. You lifted the lid and smiled at the small framed picture. You lifted it up. It was of you two and Nate. “I thought you’d like that.” He told you.  

“Thank you.” You kissed his cheek. “I love it. And you.” You said happily. 

You were getting ready for bed as Sam and Jess got ready to go. Sam grinned at Dean. “So, so you think you’ll propose for Christmas?”

“Propose?” Dean nearly choked. 

Sam’s grin fell. “Yeah, you guys act married, and have a family. I thought you’d be planning that.” He admitted. “Like I thought you might have a ring.” He went on. “Or that you’d be saving for one. 

Dean shook his head. “Nope.” He said bluntly. “No ring, no saving for one.” 

“Oh. My bad.” He said awkwardly as he spotted you. 

Dean turned. “Ready for bed?” He asked, not knowing how much you heard. He felt nervous. Would you be upset?

You weren’t sure what to say, so you simply nodded.  “Night, Sam.” You gave him a wave. 

“Night, Y/N.” He waved back and met Jess outside. “Well, Christmas is going to be awkward…” He told her. 

“So awkward.” She had overheard. “I hope this doesn’t cause issues.” She sighed. 

Sam hoped not either. He led her to the car. 

Dean got ready for bed and joined you, worried. Should he just ask if you heard? Or ignore it? He chewed on the inside of his cheek. He was confused. 

You hugged a pillow as you tried to relax. While you weren’t in a rush to get married, was that something he never wanted? Ever? Or just with you? Your stomach was in knots. Maybe it wasn’t his thing? Should you ask so you knew not to ever hope for that? 

“Babe?” He asked softly. 

“Yeah?” You breathed.

“I love you.” He reminded you. 

“I love you, too.” You let him hold you close. You knew that Nate would be waking up in a couple hours. So you forced yourself to sleep. 

Dean, however, couldn’t sleep. He felt bad. He couldn’t guess what you were thinking. He just couldn’t picture marrying anyone. Never had. He didn’t see it as important. He just hoped he didn’t crush your dreams if you heard him say that. Was that something you’d been hoping for? Dreamt of? Was he ruining things for you? He rubbed your arm as he thought. Maybe he’d mention it at breakfast? When you weren’t resting. 

Dean watched you bounce Nate. “Uh…” He loved watching you with him, and even slightly hoped for another one day. “Babe?”

“Yeah?” You looked at him.

“I’m sorry. If you overheard yesterday.” He told you softly. “I don’t know if marriage was in your plans.” He went on, seeing your eyes go to Nate instead of staying on him. “Please tell me if it was?” 

You shrugged a shoulder. “It doesn’t matter.” 

“Yes, it does.” He said gently. He didn’t like hearing you like this. “I assume it was since you’re not telling me.” He went on. 

“I wasn’t rushing into it, but maybe someday was my thought.” You said sadly. “But if it’s not your plan, I don’t want to force you.” You bounced Nate as he fussed slightly. 

Dean sighed softly. “But that hurt you to hear.” He went over to wrap his arm around you. “I’ve just never been that kind of guy.” He explained. “It’s never been something I’ve been interested in. That hasn’t changed.” 

You nodded. “I wouldn’t force that on you.” You repeated. You kept your focus on Nate. 

“Doesn’t mean I don’t want to be with you.” He said softly. “I promise you that. I love you, and I love being with you.” He kissed your head. “I’m committed to you.” He held you close with one arm, and ran his free hand over Nate’s head. “I love our family and I have no plans of ever leaving it.” He hoped you believed him. 

You nodded. “Okay.” You whispered. What else could you say? That’s just how it is. You loved Dean, and wanted to be with him, so you would have to forget your hopes of ever getting married. That’s all. It would probably just take time. 

Dean kissed your cheek. “Thank you.” He said softly. “Family day today?”

“They’re all family days.” You smiled softly. . “But I’ll never turn that down. Maybe bundle him up and we can take a walk this morning?” 

“Sounds great.” He agreed. “Want me to make us breakfast first?” 

“Okay.” You agreed. “Pancakes?” You asked, moving Nate to your shoulder. 

“With honey butter?” He stood. 

You nodded. “Sure.” You watched him as he moved around the kitchen. You loved him so much. Him and Nate were your everything. You hoped you never lost him. You glanced down at the thought. Just the idea of one day losing him hurt so much. You hoped to always be enough for him. 

Dean was hoping close to the same- that you didn’t leave him over this. He hoped you felt how much he loved you. He’d have to keep showing you. Constantly. He decided to plan something perfect for Christmas. He smiled at the thought. He heard Nate sneeze and looked over. “Bless you, little man.” 

You grinned at him and wiped his nose gently. “I’ll go change him for the day.” You got up to go do that while he worked on breakfast. “Uncle Sam got you a new outfit.” You told Nate. You smiled and kept talking to him as you went to his room.

Dean took a selfie of him and Nate as he waited in line for your coffee. His phone had so many pictures of you and Nate. And he had already had to buy more storage. He decided to get some printed out for the house. Christmas was day after tomorrow. Which meant they’d likely get printed closer to the new year. Luckily he had your gifts all wrapped. One that he was so excited to give you was a necklace with Nate’s birthstone. He had almost spilled. It was so hard to not say something.  

Dean got your coffee and started walking back to your store with Nate. You were currently helping with the holiday rush. He hoped that you could relax that evening. He went in, grinning as Nate got excited to see you and Sam. “Yeah, there’s your mom and uncle, buddy.” 

You waved from where you were. “There’s my guys!” You beamed. 

Dean rushed over to give you a quick peck. “Here’s your coffee, babe.”

“Thank you. I needed one so bad.” You smiled. You took a sip and got back to work. 

Dean stayed watching for a while. “What sounds good for dinner?” He asked after bundling Nate to head home. 

“That chicken bake you make?” You asked. “That sounds so good.” 

“Sounds great, babe.” He nodded. “Love you.” He waved. “Bye, Sammy.” Sam gave him a wave back. “Let’s go, buddy.” He carried Nate out. He’d get Nate to nap, and then start working on dinner. He wondered if you’d want to start working more soon. If you did, the two of you may see each other less. So he slightly hoped you didn’t. He felt that you didn’t need to. He was able to help. And he didn’t want you to stress about childcare. At all. Especially if he wanted to bring up more. He’d talk to you over dinner. 

Dean slid over your hot cocoa. “Question.” He started. “What were your plans for work?” He asked. 

“Like, my plans for the store?”

He nodded. “Do you plan on going back for more hours?” He clarified. “After the new year.” 

“I was thinking about it.” You admitted. “But who would watch Nate?” 

“That’s what I wanted to talk to you about.” He admitted. “I want you to know that I’m okay with you working the hours you are now. I don’t want you stressing yourself out trying to work more.” He explained. “I can watch Nate like I have been.” He gave you a reassuring smile. “And more time for us.” He loved having so much time with you and Nate.

“That’s true, but I’m not contributing much.” You said. “I don’t like that.”

“You contribute a lot, even if it’s not always with money.” He told you. 

You shrugged a shoulder. “I’ll think about it.” You promised. 

“Please.” He smiled. He hoped you liked the idea of not upping your hours. What you did now worked for the best. And he felt it would benefit Nate. 

“I won’t make any decisions until after the new year.” You told him. “Deal?”

“Deal, sweetheart.” He agreed. “Thank you.” He felt that was a good time frame. “Excited for the big day?” He looked to where Nate was. 

“I’m so excited to spend it with him.” You nodded. . “I can’t wait until next year, though, when he can really get excited.” You grinned. 

“When he can tear up wrapping.” He chuckled. “That’ll be cute as shit.” 

You giggled. “It will.” You agreed. “All the pictures!” You said excitedly. “We’ll see more of his personality.” You really couldn’t wait. Especially cause you knew he’d take after Dean. In a couple years, you’d have a tiny Dean running around. 

“Did you want more? Down the line?” He asked suddenly, making you choke on your drink as you took a sip. “Sorry.” He said instantly. 

“Don’t be. I was just surprised.” You told him. “You want more?” You asked, having not expected that.

“Yeah.” He blushed slightly. “I really would.” 

You shyly smiled. “I had no idea.” You hadn’t thought about it too much, but you thought he’d be a one and done kinda guy.

“You make me want those things.” He smiled. “I’d love at least one more.” 

You smiled wider. “We can plan that.” You chuckled at the look on his face. It was adorable. “You’re a great dad.”

He looked shy instantly. “You think so?” He felt he’d always be worried about that. 

“I know so.” You said firmly. “Nate loves you.” You assured him. “He gets smiley when you’re there.” 

Dean smiled. “I hope to always be great.” He looked to Nate, then back to you. “You’re the best mom.” He said, voice full of love. “So lucky to have you.” He went on. 

You shook your head, blushing. You were still shy with his flirting.

He grinned, loving that. He hoped to always make you feel that way. 

Dean handed you your last gift. “Saving the best for last.”

“Dean you’ve already gotten me so much.” You protested. 

“You gave me Nate sooooo…” He grinned. “I have years to make up for.” He said it like it was nothing. 

You shook your head and opened the box. “Oh, it’s gorgeous!” You touched it gently. “Dean!” You lifted it from its box. 

“And we can add to it later on.” He winked. “Made sure we could do that.” He chuckled as you blushed. 

“Help me put it on?” You asked him. 

Sam and Jess shared a look. Christmas wasn’t as awkward as they thought it would be. They were relieved. Maybe you didn’t want marriage, either? That would be a good fit. Sam kissed the top of her head, looking forward to giving her his last gift. She beamed up at him and pecked his cheek. She was so glad that they met. She sort of had Dean to thank for that. Had he not moved to town, she never would have met him. 

Sam handed her a gift bag cutely. She took it, wondering what it could be. She pulled out the tissue paper and gasped. Her eyes went to Sam, you was grinning. He cupped her cheek gently and slid down on to the floor on one knee. “Jess…” He started, a bit nervous. “I’m pretty sure I knew you were the one, the second I saw you.” He told her. “And then I had to go back to school to finish up, and I felt like I was missing part of me.” He told her lovingly. “I never want to be without you. Can I be your husband?” He decided to ask that way instead of the usual ‘will you marry me’ bit. 

She nodded tearfully. “I’d love for you to be my husband.” She pulled him into a kiss. 

You clapped, happy for your cousin. They were so good together. You went to hug her as Dean hugged Sam. “I’m so happy for you!”

She hugged you tight. “I was so surprised!” She chuckled. She looked so happy. You loved that for her. 

“Dude, you didn’t tell me your plan!” Dean chuckled at Sam. 

“Wanted it to be a surprise for everyone.” Sam was over the moon. He smiled at you and Jess as you looked at her ring. 

Dean patted his back, watching too. You looked so happy for Jess. His heart thumped. He couldn’t help it. He loved your smile. He loved everything about you. He smiled when you smiled at him. Sam nudged him. Dean nudged him back. “What?” He asked. 

Sam smirked. “Nothing.” He chuckled. “You’re whipped.” He teased.

“So are you.” He countered. “So shush.” 

Sam chuckled, agreeing. He wasn’t wrong. He loved Jess so much. He couldn’t wait to marry her. He was glad he surprised her. It had been so hard not to just blurt it out. She seemed to like the ring. He had tried to find something that made him think of her. 

“Excited to tell mom?” Dean asked. 

“I am.” Sam nodded. “She really likes Jess.” He said proudly. “I think mom and dad will both be excited.” 

“At least.” Dean knew his dad would never accept it for him. Which bothered him more for you than for himself. He shook his head at the thought. At least his mom liked you. A lot. He was jerked from his thoughts as he heard Nate. 

You bounced Nate as he was up from his nap. “Was that some good sleep?” You tickled him gently. “Hungry?” You went to help with that. “Then you can get some daddy cuddles.”

Dean brightened at that. “I’ll take those cuddles whenever I can get them.” He looked at Sam. “You guys planning on having?” He asked him, seeing Sam as wanting at least a few.

“We haven’t talked about it.” He admitted. “Maybe in time.” He smiled. “We like being aunt and uncle.” He told him honestly. 

Jess came over and hugged Sam’s side. She kissed his cheek happily. 

“Happy for you guys.” Dean nodded. He knew that you’d probably be in the wedding. That excited him. You’d look beautiful. He beamed once you came in. “Hey, babe.” He said happily as you gave him Nate. “How’s our little guy?” 

“Great now that he rested.” You kissed his cheek. You touched your new necklace and smiled. You thought it was such a sweet gesture. It would always remind you of Dean now. 

He saw you playing with it and grinned. He was so happy. “Can’t wait to add to that.” He said softly. 

You blushed. “Same here.” You agreed. “Maybe in a couple years.” You noted. “Give us time with Nate.” 

“You guys are planning another?” Jess grinned. “We get to be an aunt and uncle again?” She asked. 

You nodded, giggling. “I was surprised when Dean asked. I choked on my drink.” 

“Dean’s a softie.” She grinned. “We all know it.”

“Yeah, yeah.” Dean chuckled. “I just like being a dad.” He said proudly. He looked at Nate as he stretched. 

You had helped Jess plan everything she wanted. It had been six months of planning their wedding. It was coming together beautifully. You couldn’t wait to watch her say ‘I do’. You helped her dress on the big day, with Mary. “Excited?” You asked her. 

“So excited!” Jess smiled. “I’ve been counting down.” She said happily. 

Mary beamed. “We are so happy for you.” She helped her fix her veil. “There. All ready.” She couldn’t wait to see Jess and Sam get married. She walked out with you and smiled. “Maybe one day this will be you and Dean.” She smiled at you.  

“Maybe. I don’t think Dean is the marrying type but that’s okay.” You smiled. “We still have a cute family.” 

“Never know.” She chuckled as you both went to your spots. She felt she could see Dean marrying you. But either way, she was glad you two seemed to love each other very much. Today was for Jess and Sam. 

Dean stared when he saw you and couldn’t stop smiling. You looked beautiful. “You’re so beautiful.” He whispered as you walked down the aisle to your spots. 

“Thank you.” You grinned. He looked so handsome. You loved seeing him all dressed up. 

The wedding was beautiful and your cousin looked so happy. She teared up as she said her vows to Sam. She loved him so much. 

Finally, they were declared husband and wife. You and Dean cheered so loudly.  You were both so excited for your family members. The party would be amazing. Everyone looked forward to the reception. 

You smiled as Mary danced with Nate in her arms. He was a giggling nine month old. John slid up beside you and held out a drink. “Oh, thank you.” You took it. 

He nodded. “Enjoying yourself?” He asked. 

“I am. I’m so happy for them.” You grinned. 

He nodded, watching Mary. She loved being a grandmother, and looked forward to seeing Ben. “I’m no good at apologies…” He told you. 

Blinking, you looked at him. “What?” You asked, confused. 

He winced. “I’m sorry I’ve been weary about you and Dean.” He went on. “I can see how much you two love each other.” He said honestly. “So, I’d like to come around more.” He wanted to be a better grandfather. 

“Thank you.” You said after a moment. “That means a lot.” You nodded. “You’re always welcomed.” You smiled. “I’m sure Nate would love that, too.” 

He grinned automatically. “He’s getting so big.” He shook his head. “A mini Dean.” He chuckled. 

“He is.” You agreed with a loving smile towards your boyfriend. “It’s adorable.” Dean winked at you as he came over. “Hi, handsome.” You greeted him. 

“Hi, beautiful.” He beamed. He wrapped his arm around your waist. “Being nice, dad?” He asked, holding you protectively. 

“He is.” You assured. “Even brought me a drink.” 

Dean looked surprised but was glad his dad was finally coming around. He smiled as his mom brought Nate over and the infant reached for him. “Hi, buddy.” He said happily. Dean was so glad he came to live in this town. He’d always be thankful, as it gave him you and Nate. “Having fun with Grandma?” 

Nate grinned at him before pointing to the lights. They were twinkling. 

John took Mary to dance, leaving you three. “You look beautiful.” He told her. 

Mary chuckled. “You look lovely, too.” She smiled up at him. 

Dean bounced Nate slightly. “Doesn’t mommy look beautiful?” He tickled him. “The most beautiful person in the whole world, huh?” He grinned. 

You blushed at that. “Dean…” 

“It’s true, babe. I’m so lucky to have you.” He beamed. “Thank you for giving me a chance.” He said lovingly. “You could have anyone, and you want me.” He shook his head. “Best feeling ever.” He’d never stop wanting to thank you. “I can’t wait for our future.” 

Your cheeks were on fire, and you couldn’t stop smiling. “I can’t wait either. I love you.” You kissed Nate’s cheek as he looked at you. “And I love you, too.” You told your son. “So much.” He grinned at you.