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I stood in front of the mirror in my room, checking over my appearance one last time. I’d spent over an hour getting ready – longer than I had expected, though I’d thankfully started getting ready early just in case – and I was happy with the result of my efforts.
I kept my makeup simple, not wanting to overdo it, but also wanting to put in some effort. I put on a light layer of foundation and added a hint of blush to my cheeks. I used eyeliner and mascara, and finished off the look with some lipstick, brushed on with my finger to get a less intense color.
I was wearing a navy blue dress that went to just below my knees. The v neck was cut just low enough to still be considered modest. The sleeves were short with a bit of lace in the shoulder and the dress was well-fitted in the chest and waist, becoming looser and more flowing at the hips. I paired the dress with my favorite heels, a black pair with simple ankle straps.
My hair had taken a bit of trial and error. I’d found a style I really liked online and it was simple enough to replicate, but it took a few attempts for me to be satisfied with the result. I rarely had a reason to do anything more complicated than throwing my hair into a ponytail, so I was possibly being a bit overly picky. I had a small braid going down the left side of my head, tucked into a twisted bun in the back.
My heart was beating a little faster than normal and I had a minor case of butterflies in my stomach. I don’t know why I was nervous. It was just Dean. We spent a lot of time together and I was more comfortable around him than anyone else. And despite what my appearance might suggest, this wasn’t a real date. It was just two friends, spending Valentine’s Day together rather than being alone. A friend date. Dean had suggested it out of the blue yesterday while we were in the kitchen eating lunch.
“You and I should do something tomorrow,” he said before taking a big bite of his sandwich.
“Ok,” I agreed easily. We were in between cases and Sam had a date with Eileen, so I was happy to spend some time with the older Winchester. “What did you have in mind? Movie marathon? Meticulously go over Baby and make sure she’s spotless? Maybe hit up a bar for some karaoke?”
“First of all, Baby is already spotless. Do you think I don’t take care of my car?” He asked in mock offense.
“What was I thinking? I’m so very sorry for having the audacity to suggest your car wasn’t perfect,” I teased, eliciting a laugh out of Sam.
“I meant we should do something tomorrow night,” Dean clarified.
“Ok… and movies or a bar aren’t acceptable night time options?” I asked.
“Not on Valentine’s Day,” he said.
“Why not? It doesn’t have to be any different than any other night we hang out. It’s not like it’s a date,” I told him.
“Who says it’s not a date?” He asked seriously. Sam coughed and got up to start washing dishes.
“Um…” I started, not sure how to respond. Dean and I had been good friends for years. There’d never been any indication he might want something more. It wasn’t something I’d ever even considered. “You’re asking me out?” I finally asked.
“Yeah. Why not? It’s Valentine’s Day. There’s no rule that says you can’t spend it with a friend. I don’t want to sit around at home. Neither of us has a date, so let’s do something together. I mean, come on, even Sam has a date!” he told me, ignoring Sam’s indignant response.
“So,” I said, wanting to make sure I understood what he was asking. “What you’re saying is, you want to go on a date. But just as friends?”
“Exactly. A friend date. It’ll be fun,” he said confidently.
“Ok,” I agreed as I got up to help Sam finish with cleaning. “I mean, like you said, I don’t have any other plans.”
“Wow. Try to tone down the enthusiasm a little bit. Wouldn’t want you to hurt yourself,” he teased.
“Sorry,” I apologized, catching the hint of genuine hurt in his words. “You’re right. It will be fun. I always like hanging out with you.”
“When I say date, I mean it,” he warned me. “That means getting dressed up and going somewhere nice.”
“Noted. I’ll plan accordingly.”
Which led to now. I was sitting on the bed, just finishing putting my shoes on, when there was a knock on the door.
“Just a second,” I called, quickly grabbing my coat out of the closet before opening the door. As expected, Dean was on the other side. He was looking very handsome in a suit and tie. What I wasn’t expecting was the bouquet of roses he held out to me.
“Dean, these are beautiful!” I exclaimed as I took them from him. He even had them in a vase already. “Thank you!” I set them on my nightstand before turning to give him a hug.
“Why do you seem so surprised?” He teased as he hugged me back.
“Well you’re not exactly the ‘get a girl flowers’ type of guy usually,” I pointed out. “And even if you were, I still certainly wouldn’t have been expecting them.”
“I told you we’re doing tonight right. Fancy clothes, nice restaurant, flowers, the whole nine yards,” he said before leading the way to the bunker’s garage.
“Speaking of fancy clothes,” he added, “did I mention how beautiful you look tonight?”
“You did not,” I answered with a small smile.
“Y/N, you look very beautiful. I’m going to be the envy of every man in town,” he said with a wink.
“Thank you,” I said, genuinely flattered by the compliment. “You look very nice too. I might need to bring a gun along just to fend off the ladies.”
Dean laughed.
“Then I’d better bring along a baseball bat. Looking like that and capable of using a gun? The guys won’t be able to control themselves.”
We’d reached the Impala and Dean opened my door for me, waiting for me to get settled before closing the door and moving around to the driver’s side.
“Where are we going?” I asked as Dean expertly maneuvered the Impala out of the garage and onto the road.
“Olive Garden,” he answered.
“Really?” I asked, surprised. It wasn’t a place I would imagine him ever picking.
“All right, so it’s not that fancy. But we’d probably have to drive for a while to find an actual fancy restaurant,” he said, defending his choice.
“I wasn’t complaining,” I told him. “It sounds great. I just wasn’t expecting you to choose a pasta restaurant.”
“I thought you might find it to be a nice change from all the burgers we eat,” he explained.
“I’d be happy with anything. Although we might be a little overdressed for our usual places,” I answered. He looked over at me and smiled.
“Olive Garden it is, then.”
~~~~~
There was a thirty minute wait to be seated once we got to the restaurant. We sat in the waiting area and passed the time by talking about past Valentine’s dates. I wasn’t sure how much of the sob stories Dean relayed to me of the heartbroken girls he’d gone for were true and how much he made up for entertainment value, but I was entertained either way.
Eventually the hostess seated us and the waitress came by shortly after to take our drink orders. I didn’t appreciate how close she stood to Dean or the way she batted her eyes at him. Dean asked for an order of fried mozzarella as an appetizer.
“What?” He asked as she walked away, noticing my slight frown. “Should I have gotten something different? It’s fried cheese. Everybody loves fried cheese.”
“It was a good choice,” I agreed.
“Then what’s that face for?” He wondered.
“It’s nothing,” I told him. I was probably misreading things. Surely she wouldn’t be flirting with a guy she believed to be on a date.
“Alright,” he said, not convinced but willing to let it go.
We spent a few minutes in silence while we looked over the menu.
“There sure aren’t many options for meat at this place, are there?” Dean commented.
“Well what did you expect when you picked a pasta place?” I teased with a smile.
The waitress came back with our drinks, once again standing closer to Dean than was necessary.
“Are we ready to order?” She asked cheerfully.
“Go ahead,” Dean said, letting me order first. I looked at the menu again, reading off the name of the dish I wanted. Dean gave her his order, and she collected our menus, accidentally on purpose touching Dean’s hand as she grabbed his.
“Okay, seriously, what’s up?” he asked when she was gone. I realized I was scowling at her retreating form.
“She’s awfully friendly,” I stated. His forehead wrinkled a little in confusion.
“Yeah, I guess so,” he said.
“A little too friendly,” I tried again. He just looked at me blankly. I sighed.
“Dean. She’s flirting with you big time.”
“Yeah?” He said, still not getting my point.
“So you noticed?” I asked.
“Yeah, I noticed. Kind of hard to miss. I still don’t see the problem.”
“You don’t?” I asked incredulously.
“Are you jealous?” He asked, surprised. Then, with a cocky smirk, he added, “You have no reason to be jealous when you know I’m going home with you tonight.”
“That’s not funny Dean. And I’m not jealous.” I told him.
“It’s a little funny,” he said, encouraging me to agree with him. When I didn’t he just sighed. “I really don’t see what the big deal is. So she’s flirting. It’s harmless. I’m not going to abandon you to go home with her if that’s what you’re worried about.”
“I know that,” I told him. Dean was many things, a major flirt being one of them, but he wasn’t the type of guy to ask a friend to hang out and then leave them when something better came along.
“Then what’s the problem?” He asked again.
“You and I know that we’re just out as friends. But she doesn’t. It’s Valentine’s Day. We’re a man and a woman eating together alone, all dressed up. For all she knows we’re in a very serious, committed relationship. You don’t hit on men who are in a relationship,” I explained.
“So what you’re saying is, you don’t like her because she is knowingly trying to score with a guy who, to her knowledge, is already taken?” He asked.
“Exactly.”
“I can work with that,” he said with a smile. He scooted his chair around the table so he was sitting beside me instead of across from me and grabbed my hand just as the waitress came back with our appetizer.
“Can I get you anything else while you wait?” She asked.
“You want anything else baby?” He asked me, an amused sparkle in his eye.
“No thanks,” I told him, quickly recovering from the surprise his actions and the pet name had caused.
“We’re good for now,” he told the waitress, never even looking in her direction, keeping his eyes on mine the whole time.
“Alright. Let me know if you change your mind,” she replied, her tone slightly less cheerful than it had been. She left to go check on her other tables and Dean and I both snorted out a laugh when she was out of earshot.
“Thanks for that,” I said.
“No problem baby,” he teased. I pinched his hand, which I realized I was still holding, but smiled at him.
He squeezed my hand once before letting it go. He picked up the plate of fried mozzarella, offering it to me before taking his own.
“So is there a particular reason her flirting bothered you so much, or is it just more of a general rule?” He asked around a bite.
“It’s a good rule,” I said a little defensively.
“Of course it is. I may have extremely limited experience with actual relationships, but everybody knows going after someone in a relationship is a line that shouldn’t be crossed. Obviously that doesn’t stop everybody. Which is why I wondered if maybe something happened in the past that made you a little extra sensitive to this particular situation,” he said.
“No, not really,” I told him. “I just really hate that kind of behavior. I mean honestly, be an adult. Realize that person is someone you can’t have, and move on with your life.”
After that we chatted about unimportant things. We talked about The Hunger Games , which I was trying to get him to watch. We talked about Lord of the Rings which Dean had just gotten me started on. We’d watched the first movie a few days ago and were talking about starting the second tonight. We talked about how Sam’s date might be going. Dean made a game out of guessing which couples seated nearby were genuinely in love and which were just out in an attempt not to be alone on this particular night.
We joked and laughed and just enjoyed our time together. But whenever the waitress came to our table, bringing our food or checking our drinks, Dean made sure to play it up, calling me baby, touching me in some way, refusing to give the waitress a second glance.
“Are the two of you interested in some dessert, or would you like the check?” She asked when we finished our meals.
“I’ll take the chocolate brownie lasagna,” Dean quickly answered, his gentlemanly ‘ladies first’ manners disappearing when dessert was involved.
“And,” he added, “my lovely date will take a slice of cheesecake,” he told her confidently.
She walked away to put the order in.
“What if I didn’t want cheesecake?” I asked.
“You always want cheesecake,” he answered. “You not wanting cheesecake would be like me not wanting pie.”
“Yeah, you’re right,” I laughed.
“Can I tell you something?” I asked shyly a few minutes later after our desert had been delivered.
“Of course,” he said. “Unless you’re about to tell me you’ve got a freezer full of all your Valentine’s Day dates from over the years. I’d rather not know that.”
I rolled my eyes and gave him a pleading look. This was hard to admit, but I wanted to tell him. And if he wasn’t going to take it seriously, I wouldn’t be able to say it.
“You can tell me anything,” he said, reading the shift in my mood.
“I want to say thank you for taking me out tonight. I had a lot of fun,” I told him.
“I did too. And our night’s not over. We’ve still got a three hour long movie you agreed to watch,” he reminded me.
“Of course. How could I forget?” I joked.
“Probably just too distracted by my good looks,” he theorized.
“That must be it,” I agreed.
“So really, what did you want to tell me?” He asked.
“I was actually kind of nervous for tonight,” I confessed. “I don’t know why. I’ve actually been trying to figure it out all night.”
“No luck?”
“Not really. I guess I haven’t been on a date in a while, so it’s possible that’s why. But if I’m being honest I think the more likely answer is just that it’s you.” I told him.
“What do you mean?”
“Well… you’re one of my closest friends. And even though this isn’t a real date, I guess it was just hard not to worry this might somehow change things,” I explained.
“You’ve got to stop saying this isn’t a real date,” he instructed. “You really know how to hurt a guy’s confidence. I even brought you flowers!”
“You know what I mean, Dean.”
“Yeah, I do,” he agreed, giving up on playing offended. “Even if things did change, who says that has to be a bad thing?”
“It doesn’t have to be a bad thing, but it could be,” I countered. “I just wouldn’t want something to happen that ruined our friendship is all. You’re too important to me,” I told him.
“We’re just eating dinner together, Y/N. What could happen that would ruin our friendship?” He asked teasingly.
“I don’t know. I never said it made any sense. It’s just the best explanation I can come up with for why I was nervous,” I said.
The waitress came back over with the check, which Dean took.
“Can I tell you something?” He asked me when she was gone.
“Of course,” I answered.
“I might have been a little bit nervous for tonight too,” he admitted.
He didn’t wait for an answer, just opened the folder and looked at the bill. He frowned.
“What?” I asked. “Did she give us the wrong one?”
“No,” was all he said as he fished his wallet out of his pocket. He grabbed a few bills and stuck them in the folder.
“What’s wrong then?” I asked.
“Nothing,” he assured me. He turned in his chair to fully face me and reached up, placing his hand on my cheek.
“Dean, what are you doing?” I asked. His face was inches away from mine and he was staring directly into my eyes. My heart started to race. I felt like a deer caught in the headlights. We’d never been this close and he had never looked at me like this. His gaze was magnetic. I couldn’t look away.
“Remember when you said you didn’t want things to change between us?” He asked.
“Yeah,” I said nervously.
“Just remember that this doesn’t have to change things,” he said. Then he was leaning in and pressing his lips to mine.
I responded instinctively, placing my hand on the back of his neck and kissing him back, but my mind was racing.
Why was he doing this? Had I misread things entirely? Had this really been a date? These thoughts were somewhere in the back of my mind, fighting to be heard. All I could really focus on was how his lips were such an enticing combination of soft but firm and how good of a kisser he was. The only thought I could grasp onto was that this was the best kiss I’d ever had. And it was over before it could really get started.
He broke away from me, breathing slightly uneven. I looked at him, desperately trying to regain the ability to speak when I noticed the footsteps stopping beside us. Dean handed the waitress the folder.
“Keep the change,” he said. Then he stood up, helped me put my coat on, and slung his arm around my shoulders as we walked to the exit.
We walked in silence to the car. Once there, Dean once again opened my door for me. We sat in silence until Dean pulled onto the highway, headed back to the bunker.
“You saw the waitress coming,” I said, a statement of fact, not a question.
“Yeah.”
“Why?” I asked.
Dean clenched his jaw.
“She wrote her number on the receipt,” he told me.
“Okay,” I said, waiting for more. That bit of information irritated me more than I cared to admit, but I didn’t see the relevance.
“I made it pretty clear that I wasn’t interested, didn’t I?” he asked rhetorically.
“You did,” I agreed anyway.
“So why was she so persistent? Why did she think giving me her number was a good plan?” he asked frustratedly.
“I figured you’d be thrilled. She was pretty. I don’t understand why you’re so upset,” I said.
“Aren’t you?” He asked incredulously.
“Of course! But I’m the one who had to watch my date get hit on all night.”
“Exactly! And I am offended on your behalf. Who does that? What gives her the right to try and get into the middle of what she can only see as a happy relationship?” he fumed.
“Well you know I’m not going to disagree with you on that,” I told him. “But it still doesn’t answer my question.”
“Doesn’t it? I think that covers it pretty well,” he disagreed.
“No. It doesn’t,” I insisted. “It explains why you’re mad but not why you kissed me.”
He looked away from the road for the first time, glancing at me with steel in his eyes.
“I’d say I’m sorry, but I’m not,” he said, eyes back on the road.
“I wasn’t looking for an apology,” I said pointedly.
I could see his jaw moving back and forth, him grinding his teeth together. I waited for him to sort out his thoughts and give me an answer.
“I guess I just wanted to make a point. To really show her that I wasn’t interested,” he finally said.
We were quiet for a while as I thought about what to say. My mind was still racing. From the kiss, yes, but also just replaying the whole night. I was going back and analyzing myself. The things I’d thought and said and done. And I was coming to a realization.
I liked Dean. I liked him in a ‘more than friends’ way. I was in love with him. How had I not realized?
I remembered the nerves I felt earlier this evening while I was getting ready, apparently a physical manifestation of the feelings I’d buried so deep, I’d hidden them even from myself. I was nervous about going on a date with the man I loved. Our first date.
I remembered the irritation I’d felt at our waitress, apparently more than just the indignant annoyance I thought it to be. It was jealousy, as Dean had joked it was.
I remembered how eagerly I had agreed to keep the night going with a three hour movie. And I remembered the giddy feeling I didn’t even realize I felt when Dean called me baby and put on an act for the waitress.
Even my dress, I realized, had been picked specifically for Dean. I knew he was partial to this color. I couldn’t believe how blind I had been to my own feelings.
Dean sighed.
“Please tell me things aren’t going to be weird between us now,” he said anxiously.
“It’s not going to be weird,” I assured him, willing myself to make it true. I suppose now I have to look forward to a future full of unrequited love. It would suck, but I would make sure it didn’t impact our relationship.
“You sure? Because we’ve never really been the awkward silence type, but this car ride has been full of it.”
“Sorry. I wasn’t trying to ignore you. I was just thinking,” I told him.
He glanced at me again.
“About what?”
“Just… how much fun we had tonight,” I lied, hoping it would lighten the mood a little bit.
“Yeah,” he agreed, clearly not believing me but going along with it anyway. “Yeah, we did have a lot of fun."
Dean pulled off the highway onto the gravel road that would take us to the bunker. Just a few more minutes and we’d be home.
“We’re still gonna watch Lord of the Rings, right?” I asked him.
He looked at me, a little surprised and a little relieved.
“If you still want to, then yes,” he said.
“I still want to,” I answered.
We were quiet for the rest of the short drive home. Dean parked in his usual spot in the garage and shut the Impala off, but didn’t move to get out. I sat with him, waiting. He seemed to be thinking about something, brow furrowed and thumb tapping on the steering wheel.
After a minute or two, he seemed to come to a decision. He turned to look at me, shoulders set in determination.
“I wasn’t planning on doing this, but since I’ve already gone and made things weird, I may as well. Go big or go home, right?” He said with a rueful smile.
“I told you things aren’t weird,” I told him.
“Y/N, you’ve been looking at me differently since we left the restaurant,” he argued.
I unsuccessfully fought the blush rising to my cheeks.
“How would you know how I’ve been looking at you? You’ve been driving,” I pointed out.
“I can still see you. Anyway, that’s not the point,” he said, steering the conversation back to where he wanted it.
“Yeah, but I don’t want you to feel like-”
“Can you just let me say this? Please?” he cut me off. I sighed, but nodded.
“First of all, I know I said earlier that I’m not sorry about the kiss. And, as far as the waitress is concerned, I’m not. But I feel like it maybe made you uncomfortable, and for that I am sorry,” he started.
I was surprised at how badly he was reading me. He thought it made me uncomfortable? He couldn’t be further from the truth. I let him continue though. I’d correct him later. Or, I’d assure him I wasn’t uncomfortable at least. He didn’t need to know how much I’d enjoyed it.
“Secondly…” he took a steadying breath before continuing. “Well, to be blunt about it, I kissed you because I wanted to. It might’ve been the waitress that pushed me to it, but I wanted to. Because I have feelings for you, Y/N. I love you. I have for a while now.”
My breath caught at his admission. I couldn't believe this. In under an hour I’d gone from having a fun night with my best friend, to realizing I was in love with him and resigning myself to a lifetime of pining, to being told he felt the same.
“And like I said,” he went on, “I wasn’t going to say anything because I didn’t want to make things weird between us, but since I’ve already done such a spectacular job of ruining that-”
I cut him off the only way I knew how, in the only way I knew would convince him he had no reason to worry. I leaned forward and kissed him.
His response was immediate, wrapping his arms around my waist and pulling me closer, opening his mouth to deepen the kiss. I wrapped my arms around his neck and got lost in the feel of his lips against mine.
Eventually – seconds, minutes, hours later. I didn’t know – he pulled away. He didn’t go far, resting his forehead against mine. We were both breathing heavily.
“You know why I’ve been looking at you differently?” I asked him. He just looked at me, waiting for my answer. “It’s because I love you. I have for a while,” I said with a smile, repeating his words from earlier. “I didn’t realize it until tonight. But I’ve been going over things in my head, mostly from tonight, and it’s the only conclusion I could come to. I don’t know how I missed it for so long,” I said a little sheepishly.
“That’s ok,” he grinned at me. “I didn’t realize at first either. Sam is actually the one who pointed it out to me a few months ago. I’ve been worried ever since that I was going to do or say something that would make it obvious and wreck our friendship.”
“So this date tonight…” I trailed off. He knew what I was asking.
“I really meant it to be a friend thing. Since neither of us had plans and we’d probably have ended up hanging out anyway, I figured why not just go out?” He explained.
“Why not?” I echoed with a smile.
“I’d be lying if I said the idea of spending the night with you, all dressed up, no guys coming up to flirt with you because they’d know you were taken wasn’t extremely appealing to me,” he admitted.
“And then when you opened your door and I saw how beautiful you looked, I couldn’t believe my luck.”
“I’m the lucky one who got to go home with the best looking guy in town,” I teased.
He smiled and leaned in for one more quick kiss before getting out of the car. He came around to my side and helped me out. We walked to my room, his arm around my shoulder.
“Why don’t you change into something more comfortable and then we’ll watch that movie,” he said once we reached my door before heading in the direction of his own room.
I stood there for a while, debating what to wear. We were technically continuing our date. I still wanted to look nice. But I didn’t really have many options that fit into the category of both nice and comfortable.
Finally I decided I didn’t need to impress him. I’d been living in the bunker with them for three years now. Dean had seen every possible side of me. He’d seen me at my best and he’d seen me at my worst, both physically and emotionally. He knew everything there was to know about me, and he wasn’t running away. He wouldn’t care what I wore.
I slipped on a pair of shorts and a t-shirt, the outfit I would probably be sleeping in tonight. I wiped the makeup from my face, not wanting to forget to do it before bed, but left my hair up. Ready to spend another few hours with Dean, I made my way towards “The Dean Cave,” as he liked to call it.
I must have taken longer than I realized to decide on what to wear. When I got there, Dean was waiting for me. He was wearing a pair of soft, worn sweatpants and a t-shirt. He had the movie up on the screen and a big bowl of popcorn sitting in his lap.
He smiled when he saw me and patted the seat next to him. I sat beside him, putting my feet up onto the couch and leaning into his side. He responded by putting his arm around my shoulder. I let out a happy sigh. This was everything I never realized I wanted.
~~~~~
We were about an hour into the movie when Sam came home. He stopped in the cave, probably hearing the movie on the way to his room. He raised an eyebrow when he saw us snuggled up together on the couch.
“Hey, how was your date?” Dean asked his brother cheerfully.
“It was good,” Sam said, not giving any more detail. “How was yours?”
“Good,” Dean said.
“Uh huh. Care to share anything more?” Sam asked, clearly very curious.
“Do you?” Dean countered.
“I’m sure your date was way more interesting than mine,” Sam deflected.
“Your date with a girl you really like on Valentine’s Day was less interesting than two friends going out?” I scoffed.
“And how did that go?” Sam asked again.
“Good. Like I said,” Dean shrugged.
“Just a normal night? Nothing out of the ordinary happened?” He continued in a tone that implied he knew something he wasn’t telling us.
“Nope,” Dean and I said together. We weren’t going to keep it a secret. There was no point in even trying in such close quarters. But we both naturally responded to his knowing tone with denial, not wanting to give him the satisfaction of being right just yet.
“Okay,” Sam said nonchalantly, backing towards the door. “Hey Dean, by the way, I’d go with a different shade of lipstick next time. That’s not really your color.” With that, he left the room.
I looked at Dean. There was a little bit of lipstick smudged on his upper lip. I was surprised Sam had even noticed it. He was observant though, and if he knew about Dean’s feelings, he’d probably been actively looking for signs that things had changed between us.
“Sorry,” I said as I tried to rub it off with my thumb.
“Don’t worry about it,” he said, unconcerned, taking my hand in his and pressing play.
We finished the second movie and put the third one in. It was already late, but we had nowhere to be tomorrow and were content to spend the night curled up with each other, enjoying this new closeness.