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Dean and Castiel met when Cas was having car troubles and needed to take his vehicle to the shop. He ended up bringing it to Winchester Auto Repairs, where the mechanic flirted with him the whole time. Castiel didn’t mind though, the mechanic was pretty hot and he’d be lying if he said he didn’t flirt back a bit. He ended up giving the guy his number before he left, which is not something he does very often, but hoped to hear from him soon. It had been a long time since Castiel dated, and this guy seemed nice, was attractive, and actually showed interest in him. Later that night, alone in his apartment, he felt like a giddy school girl awaiting a text from a crush and to his delight, he got it!
Dean: hey cas it’s dean from the auto shop. i’m really hoping this is the right number cause the note you gave me was a little hard to read. anyway i was wondering if you’d like to go out to like dinner or something some time?
Cas: I would love to go to dinner with you Dean, how does Friday at 7 sound?
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Dean was so excited when he got home from work that day. He was ready to tell his roommate Charlie about the cute guy who he’d been chatting up when he opened the door, only to be greeted by a small three year old child attacking his leg in a hug. Ben did this almost every single day and Dean loved it, couldn’t get enough of it even. Bending down he picked up his son, spun him around once, and then put him on his hip. “Hey buddy! How was your day? Were you good for auntie Charlie?” He asked, smiling at Ben.
“Yes! We made cookies today Daddy! Charlie even let me help mix everything together. And guess what?” The boy said, oozing with enthusiasm.
“What?” The father asked, playing along with equally as much excitement.
“We even made extra cookies for you to take to work with you so you have a snack!”
Suddenly Charlie appeared from the hallway, “Was all his idea. Little sweetheart thought you might like to put some in your lunches and I told him it was a great idea.” She said walking over and planting a kiss on Ben’s forehead.
“Thank you bud, that was really nice of you. I’ll make sure to bring some with me tomorrow.” He said giving his son a hug and then setting him down.
The three went about the rest of the evening as usual. They made and ate dinner, watched a Disney movie afterwards, Dean played with Ben in his son's room for a little bit, then gave him a bath, read him a story, and tucked him in for bed. Once Ben was asleep, Charlie and Dean usually watched an episode or two of Game of Thrones before they themselves called it a night. Tonight however, Dean was distracted by his phone as he texted Castiel. They were barely into an episode before Charlie had to pause it when curiosity got the best of her.
“Ok spill. Who are you texting, and how are they more important than the queen of dragons?” Dean could tell she was a little annoyed, but he still couldn’t wipe the smile off of his face.
“His name is Castiel. We met at the shop today, and he’s really cute and kinda awkward but in an adorable kinda way y’know. He gave me his number and now we’re texting and I asked him on a date and…. Shit! Charlie please tell me you don’t have plans Friday cause I really wanna go on this date and I need someone to watch Ben an-”
“Woah woah woah, chill dude!” The redhead told him after he started rambling. “Even if I did have plans, which I don’t, I would definitely cancel them! Holy shit man, you haven’t been on an actual date since before Ben was born. I’m so proud of you for getting out there again.” She said and then started to hug him.
“Thanks Charlie, I’m a little nervous if I’m being honest… I don’t wanna screw this up.”
“You won’t, I have faith in you. Now tell me more about the man who has made you wanna date again, but quickly because I wanna get back to watching Daenerys being hot.” So that’s just what Dean did. He told her about Cas, they finished their episode, and the day was done.
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By Friday, both Castiel and Dean were eagerly waiting to meet up for their date. They decided that Dean would drive to pick Cas up, and they would go to dinner at a nice little Italian place that wasn’t too fancy. They talked, learned a lot about each other, and started quickly falling for one another. Once they were done with dinner, they still didn’t want the date to be over, so they left the restaurant holding hands and walked back to Dean's car, having decided to go glow in the dark mini golfing as per Castiel’s request. It ended up being one of the best nights of their lives, making memories they’d never forget. Once the date was over, Dean dropped Cas back off at his apartment but they both stalled in the car once they arrived.
“I had a really good time tonight Dean.” Cas said, not quite whispering but with a tone that was softer than normal. Chancing a glance up at Dean, he saw the green eyed man was staring right back at him. Dean reached his hand over, cupping Cas’ cheek.
“I did too,” he whispered “and I’d really like to do this again.” They both started to lean in, Cas gently closed his eyes while Dean continued to stare at the other man's lips. After what seemed like a lifetime, their lips met in the middle for a soft, slow, tender kiss. The kiss felt like it lasted forever, and neither of them wanted it to end. After a while they pulled apart, said their goodbyes, and went their separate ways. Both men were beaming and swimming in happiness, barely able to make it another hour without texting the other.
When Dean arrived back home that night it was late and the house was silent. He quietly walked into Ben’s room to give him a quick kiss on the forehead and pull the blankets up to cover him a little better. He then proceeded to go to his own room and text Castiel until he fell asleep.
In the morning he filled Charlie in on everything that happened the night previous. Talking nonstop while they both moved around the kitchen making breakfast.
“This guy really makes you happy, huh?” She said grinning, noticing once again that Dean still could not wipe the smile off of his face.
“Yeah, he does. We already have a second date planned for next weekend. I mean if you can watch Ben again we’ll have a second date, if not I can stay home with the little dude and reschedule with Cas.”
“Oh so you told Cas about Ben! That’s great, and he’s okay with you having a kid, I assume right?” Charlie asked, knowing one of Deans biggest problems with getting back into the dating world was Ben. Not in a bad way, Dean was just protective of his son. He didn’t find it necessary to tell a date about Ben if they weren’t serious. He also knew that some people just weren’t down for dating someone with a kid.
“No, uh, I didn’t tell him about Ben yet, but I really want to. I think Ben would love Cas if they ever got to meet in person. I mean the guy’s a second grade teacher so obviously he’s good with kids. I kinda just chickened out of telling him ‘cause I got scared he’d stop talking to me if he knew.” Dean said turning back to what he was doing.
“If he stops talking to you because you have a kid, was he ever really worth it in the first place?” She asked, placing a comforting hand on Dean’s arm.
“Yeah you’re right. I’ll tell him. Thanks Charlie.”
But that didn’t happen. They went on their second date, then third, fourth, and soon enough they’d been dating for almost six months and Dean still hadn’t told Cas about Ben. It’s almost absurd how long this had been going on with not one mention of the fact that Dean had a son whom he loved very much.
They were having another date night, this time at Cas’ apartment where they were having a movie marathon after a nice dinner that Castiel prepared. This would be the first time they had spent the night together, as this was the first serious relationship either had had in a long time and they didn’t want to screw it up by taking things too fast.
They were cuddled together on the couch, Cas had his arm wrapped around Dean and Dean was laying on Cas’ chest. Both enjoying the movie in the presence of the other, when Dean’s phone started ringing. Picking it up, he saw it was Charlie and instantly got up. “I gotta take this, sorry Cas, I’m just gonna go in the other room real quick.” He said before shutting himself in the bathroom. “Hey Charlie, what’s up? Everything ok?”
“No, Ben woke up puking like two hours ago and I can’t get him to calm down or stop crying. I took his temperature and he’s running a high fever. He really wants you right now Dean and I don’t know what else will calm him down. I don’t wanna ruin your time with Cas but I think you need to come home” Charlie frantically let out from the other end of the phone.
“Shit, okay yeah I’ll come home. Can you put him on the phone real quick?”
“Yeah of course.” She said. In the background Dean could hear his son sobbing and it broke his heart. He heard the sobs dull down just a little when Charlie asked if he wanted to talk to Daddy though. He knew his son said yes because in the next couple moments, Ben was on the phone.
“Daddy, want you to come home. Feel icky an’ I want you.” His son spoke through tears that he was trying to hold back in order to talk.
“Yeah I know baby, and I’m gonna come home to you alright, really soon. I love you Ben, you think you’ll be ok until I get home?” Dean felt his eyes well with tears at how upset Ben was.
“Yes, you please hurry. My tummy hurts an’ I miss you.” A tear slid down the father's face as his son continued to plead for him to come home.
“Yeah sweetheart I’ll hurry, see you soon, I love you.” Ben uttered a quiet ‘love you too’ and then they hung up. Dean knew that he’d now have to tell Cas about his son, and quickly so he could get home to his baby boy. Trying to compose himself, he wiped his face, took a deep breath and headed back out to the living room. When he got out there though he was truly surprised to see that Castiel also had tears in his eyes, and even a few streaming down his face.
“Hey uh, I don’t know why you’re upset but I-”
“You don’t know why I’m upset? Are you kidding me Dean?” Cas shouted, “I think you need to leave, if I’m not mistaken, and I’d appreciate it if you didn’t come back.” and with that, the shorter man walked to his bedroom and slammed the door shut, all before Dean could get another word in.
Dean was left shocked and confused, but left anyway to get to his son. He would have to text Cas later to ask what the hell that outburst was about.
When Dean got home Ben was still crying. As soon as he realized his Dad was home though, he was in his arms in an instant. “Daddy I missed you. My tummy hurts so bad I can’t sleep an’ all I wanted was you to hug me but you were gone!” His son sobbed into his shoulder, embracing his father in a tight hug.
“Shhhh, Ben. It’s alright you’ll be okay, I’m home now. How about we go lay down in my bed? Does that sound good?” He whispered, rubbing his sons back soothingly.
“Mhm” The little boy hummed while nodding his head. They went to Dean’s room and cuddled together on the bed. Dean gently rubbing the boy's belly hoping to sooth him. It must have worked, as Ben fell asleep in less than five minutes, that mixed with the comfort of having his Dad back and wearing himself out with all the tears. Dean also fell asleep quickly, deciding to just text Cas in the morning.
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Castiel woke up with a headache as he had spent his night crying himself to sleep. He really loved Dean, and had it in his mind that Dean also loved him back. But no, dating has never worked out for Cas before, why should it now. He couldn’t get over how stupid he felt though. Here he was thinking Dean was the one for him, only to find out he’s been cheating for who knows how long! Leaving Castiel heartbroken and alone.
When he grabbed his phone from the nightstand however, he was not expecting any texts from the man himself.
Dean: hey i know i left pretty quick last night and i’m sorry about that. i really had to get home it was a little bit of an emergency
Dean: i was also wondering what was up right before i left? did something happen? like are you ok?
Was he for real? Did Dean seriously not get why he was upset?
Cas: I’m sorry you had an “emergency” to attend to, but I would like if you stopped texting me. You don’t need to lie or pretend anymore Dean. I heard you on the phone last night with Ben. If I didn’t make it clear enough yesterday, we are through Dean Winchester. Please do not try contacting me again.
And that was that. He threw his phone onto the end of his bed, and moped his way through the day.
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Dean was up bright and early with a pukey child. Ben’s fever hadn’t gone down yet and he still felt “icky” as he said. He let Charlie sleep in and tried to make his son some oatmeal, hoping it would stay down. In the midst of his morning he texted Cas briefly about the night before.
He was sitting on the couch watching cartoons with Ben on his lap when he finally got a response from Cas. What he got though, was nowhere near what he was expecting. Cas was breaking up with him… because he heard Dean talking to his son. He never could have seen this coming, genuinely thinking that Cas would be more than okay with Ben. If Dean had known this is how Cas would react to Ben, he would’ve called it off a long time ago. But no, he had to go and get all attached to the guy.
For the next week and a half, both men went gloomily about their lives. They both missed each other but Cas could never be with a cheater, and Dean couldn’t be with someone who wouldn’t accent his son. Castiel had several of Dean's things though, because he was constantly over at Cas’ apartment, and he really wanted to get rid of them. He didn’t want to be petty about it so he figured he’d just put them in a small box and bring them to Dean. Facing him one last time before hopefully never seeing him again.
He pulled up to Deans house, stalled in the car for about five minutes, then decided to just get it over with. He walked up to the front door with the box in hand, and knocked. The door opened slowly, and to his surprise, Dean was not the one who answered the door, but neither was his roommate Charlie who Cas had heard a lot about. No, instead on the other side of the door was a cute little boy with a mop of black hair who couldn’t be older than four years old. “Hello!” The little boy said with a friendly smile on his face
“Ben! What have I told you about answering the door.” And suddenly Dean was there, having appeared out of nowhere. He scooped up the child in his arms and that’s when it hit him. Ben was not the name of a secret lover, but rather the name of a child. Cas messed up. “What are you doing here? I thought you didn’t wanna see me anymore, now that you know I have a kid.” Dean said obviously annoyed.
“A kid? Ben is your son?” Cas muttered mostly to himself as he was still comprehending everything.
“Yeah, I thought you knew that. You told me you heard me on the phone with Ben when he got sick a couple weeks ago and that you didn’t want anything to do with me anymore. Ring any bells?” Dean said bitterly, going to shut the door with the child still in his arms.
“Wait!” Cas halted, putting his shoe in the door so it couldn’t close all the way. “Dean may I please come in. I believe there has been a big misunderstanding on my part and I’d like to talk to you.”
Dean thought it over for a minute before responding. “Fine. But if you start disrespecting my kid in any way I swear t-”
“I would never. And I apologize if that's the impression I’ve given you.”
Dean opened the door and let the dark haired man in, setting Ben down in the process and bending down to talk to him. “Hey buddy, Daddy’s gotta talk to this guy real quick alright. How about you go play in your room with your hot wheels and I’ll be in soon.”
“Okay, don’t forget we’re going to get ice cream soon though. Bye Daddy!.” The boy yelled already halfway across the house, too excited that he gets to play with his hot wheels.
“How old is he?” Castiel asked.
“Three. He’ll be four in a couple months though. Makes me feel old.” Dean said. They both just stood there in an awkward silence until Cas spoke up again.
“I’m so sorry Dean. I shouldn’t have broken up with you. I overheard you saying ‘I love you’ to a Ben on the phone that night and automatically thought the worst. If you could find it in you to forgive me, I’d love to be your boyfriend again.” At this, Dean had a dumbfounded look on his face.
“Wait hold on. So you broke up with me because you thought I was cheating on you? Not ‘cause I have a kid?” There was a look of absolute bewilderment upon Dean's face, leading Cas to know that he was serious.
“You thought I broke up with you because you have a child? Dean I’m an elementary school teacher, I love kids, I would never do that.” After that they both stared at each other for a moment before Dean burst with laughter.
“Good god, we actually did that. Why are we like this?” He said still laughing but now going in to hug Castiel like he has so desperately wanted to for the past week and a half. “I’ll forgive you, if you can forgive me, then we can be boyfriends again.”
“Deal.” Cas whispered, pulling away from the hug to give Dean a soft kiss on the lips.
“Eewww” And at that they pulled away.
“Hey! Get over you little twerp.” Dean jokingly hollered to Ben who was hiding around the corner. He ran over, standing beside Dean and reaching his arms in the air, signaling he wanted to be held. Dean picked up his son and held him close. “This is Daddy’s friend Cas that I was telling you about. Can you say hi please?”
“Hi Cas! Daddy says you’re really nice. You wanna go get ice cream with us?” The young boy asked enthusiastically, smile still plastered wide across his face.
“I would love to go get ice cream with you and your dad.” Castiel said smiling right back at Ben. He then turned his gaze back to Dean and continued however, “If that’s okay with you of course. I don’t want to overstep any boundaries.”
“We would love if you could come with us Cas.”
And with that they left. Castiel and Dean were both so happy to be back together, and Ben was excited that his dad let him pick the chocolate ice cream this time.