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Whenever someone asked Castiel what he saw in the infamous Dean Winchester, it was never usually a straight answer.
One of his older brothers, Gabriel, was less interested in the relationship part and more interested in the idea that his younger brother was in love with someone with a reputation as weird as Dean’s. Gabriel was a senior by the time Castiel reached freshman year, and Dean already made himself a reputation of getting into fights with some of the older kids.
“Every time you talk about him, he sounds like a complete asshole,” His brother said mindlessly while watching some random reality TV show. “Are you sure you like him?”
As if Castiel didn’t spend the last four years absolutely crushing on Dean.
“I’m sure,” Castiel replied, grabbing the remote and changing the channel to something infinitely more interesting.
“What’s he got, anyway?”
“Hm…” Castiel pondered, he would have to put it in a way that wouldn’t make Gabriel fake vomit or even worse, find a way to make fun of him. “I guess, the way he remembers small details.”
“Corny,” Gabriel nodded, a smirk forming on his face, the one where he’s really holding back a laugh. “But, hey, if that makes him lovable, why not?”
He leaned over to Castiel and ruffled his hair, a thing he knew Castiel hated.
Dean remembered a lot of things, even things most people would have forgotten they’ve mentioned. He always remembered birthdays and small anniversaries. He showed up with gifts or light conversations, it was like he knew every detail of people he loved. He made them feel seen. When Castiel randomly mentioned he loved bees and nature, Dean showed up with a poorly wrapped gift at school on his birthday. A small bee charm for his phone, to swap out the old damaged feather charm that he talked about changing. That’s when he knew Dean was too good for him.
Anna was more than welcome to indulge in Castiel’s delusions. Afterall, they were twins, meaning that both Anna and Castiel ended up having an embarrassing crush on Dean at some point in time.
“What girl hasn’t?” She said. “I’m over it now, he’s all yours.”
“We are not dating, Anna.”
The two were sitting on her bed, during a time in which Anna liked to call it ‘tea time’, meaning a private time to share secrets and stories. Anna gave him a look. She deemed it ‘twin communication’, where she assumed Castiel knew what she meant, and true to her word, he did.
“Do we always have to talk about my crush, what about yours?” Castiel sighed, getting hit in the face by a pillow. He knocked backwards, landing on the extremely stiff mattress. He didn’t understand how Anna could ever sleep on something similar to a plank.
“I don’t have one.”
“You’re lying.”
“Why would I lie?” Anna smiled. “We tell each other everything.”
“Anna, please.”
“Please, what? I wanna listen to your corny love life stories all day,” She leaned back and fell beside him. She turned her head and Castiel did the same, they both looked at each other. “You talk about Dean so fondly, it sounds like a romance movie.”
One thing Castiel loved about Dean was how much of a family man he was. Dean didn’t care about anything more than his family, just as Castiel did. After school, Dean would invite him over, where Dean and his mom would spend hours cooking the most delicious dinner. Castiel was allowed to help… Sometimes. Dean laughed when Castiel asked if he could assist in any way. Then, Dean reminded him that he nearly burnt off his hand trying to take out something from the oven with no gloves. Castiel was reduced to playing video games with Sam while they waited, which Dean would occasionally pop in just to ‘backseat game them’.
Castiel actually spent a lot of time at the Winchester’s house, it had gotten to the point where Castiel didn’t even have to ask anymore. He even somehow managed to start getting invited to family events. Dean invited Castiel to Sam’s elementary school talent show, which Dean managed to convince him by saying it would be a blast. Of course, Castiel ended up staring at Dean in the dim lighting from the stage, but seeing Sam and Jessica sing “Crazy in Love” was another highlight of the night.
“You two are insufferable,” Uriel said, unamused. His cousin was always outright and straightforward.
Uriel always visited when he was in town, Castiel was still the bratty younger cousin to him. Though Castiel appreciated Uriel’s bluntness, it was a needed reality check.
“Why?” Castiel asked, genuinely curious. He and Dean had spent the last four years being best friends and it did have its ups and downs, but it was never horrible.
“Every time I come over, you always bring him up,” Uriel stated. “You think of him with fondness in your eyes, yet you tell me you’re only friends. I normally don’t care about these things, but you’ve gotten on my nerves.”
“I don’t see how that might be an annoyance to you,” Castiel replied. “It’s my life.”
“Your insufferable life,” Uriel added. “And your insufferable not-boyfriend boyfriend’s life.”
Honestly, Castiel didn’t give actually dating Dean much thought. They’ve hung out so much it was basically the same thing. Ms. Winchester was so kind and welcoming, Castiel wished she was his mom. Even Bobby was something he wished his father was. He and Dean spent some time in the garage with Bobby, learning how to fix tires and parts of cars.
“Ladies like a man who can fix their car,” Dean nodded.
Bobby smacked the back of his head. “And also saves you insurance money.”
Castiel stared at Dean, his eyes not being able to tear away. Even alone, he was still thinking about impressing the girls at school. He was always funny like that, whether it be Melissa for a week, or Tiffany for a day. Dean turned around and caught Castiel staring at him, a small smile forming on his face.
Walking over to the Winchester house was never a problem, a short twenty minute walk was nice on summer days. Winters were dreadful, wearing layers upon layers in slippery conditions. Dean had lightly grabbed Castiel’s overcoat sleeves, told him that he looked cute all bundled up before pushing him into the snow. Castiel knew only Dean would pull a distraction like that just to be a dick and soak all of his clothes. The two ended up having a short snowball fight, Castiel winning, he chose to ignore the fact that Dean probably let him win.
After that, they got up and talked for hours, walking on a snowy trail near Castiel’s house. It had become a yearly tradition to update each other on their lives, or say things that couldn’t be said to anyone else. Dean dreamt of being a firefighter, he stayed up late googling recipes so he and his mom would never run out of things to cook together, and he took as many hours as he could at his part time job so he could put all the money into Sam’s university tuition.
Dean slid a snow pellet across a small frozen river, talking about how he wanted nothing more than seeing Sam have a life he couldn’t. Castiel walked up beside him, standing as close as possible, feeling a tinge of Dean’s body warmth. He turned his head to look at the boy while Dean stared out onto the river.
Balthazar spun around in Castiel’s desk chair, staring up at the ceiling.
“Have you ever considered asking him out, or are you going to wait forever?” He said, bored. “I’m tired of seeing you like this.”
“What do you mean?” Castiel looked up from his book. He was sitting on his bed, reading as normal. He always appreciated Balthazar’s hang outs. They were filled with enjoying each other’s company, a nice break from their usual busy lives.
Balthazar laughed until he realized Castiel was being serious. “Really? How long will this Dean Winchester pull your heart along until one of you confesses?”
“He doesn’t like me like that,” Castiel said, quick to defend Dean.
“What about the time he didn’t hear from you in three hours so he drove everywhere to look for you?” Balthazar scoffed. “Or the time he wouldn’t leave your side in the hospital after one of your organs erupted?"
“He does that for everyone,” Castiel remarked, he did feel his face heat up a bit. “For everyone he cares about.”
“He does that for his family,” Balthazar corrected. “And you.”
“I’m his family.”
“Yeah, once Dean finally gets down on one knee and proposes-”
Castiel tossed his book and smacked Balthazar directly in the head.
How many more years could Castiel go with longing for Dean? He was more than willing to go on forever, that’s for sure. He really had no reason to think Dean had any interest in him. Dean kissed a lot of girls in janitor closets while somehow managing to flirt with everyone who has the gull to have any interest in him. Dean would never think of him like that, Castiel wasn’t some girl that had his eyes sparkle whenever they looked at Dean and he certainly wasn’t crushing on Dean just to kiss him once and forget.
Whenever someone asked Dean about his love life, he’d brush it off. Maybe he’d point out how good of a kisser he was, but ultimately, Castiel had no hint of what dating Dean Winchester would actually look like. He assumed it was sloppy makeout sessions in hidden alcoves around the school. Though, Dean surprisingly stopped kissing any girl by the time they reached senior year. He and Castiel hung out a lot more too, considering that Dean got his drivers license and now spending time walking everywhere was an afterthought. The two would spend late night hours laughing in the Impala, eating burgers and chatting about dumb things they did as kids. Castiel even believed Dean would lean too close to him while laughing.
This boy would be the death of him, Castiel decided.
Dean had called him earlier, telling him to stop by his house around 8 PM, when he would be off work. Castiel pulled on his typical overcoat and headed down the street. Summer time always meant breathtaking sunsets, and Castiel spent his time thinking about Dean instead of taking it in.
They’d be off finding jobs soon enough, Castiel would be studying business just as the rest of his family in the nearby university. Dean would be working as a firefighter, saving lives. He longed for another year, just to keep this normal routine. Castiel wasn’t so sure he was ready to grow up, if it meant seeing the Winchesters less.
“Hey, Cas!” Sam opened the door. “Dean’s not here yet… Let’s play some Call of Duty!”
“Uh, Sam, you know I’m not very good at these video games,” Castiel sighed. Sam took the sleeve of his coat, dragging him to the living room. He looked down at the controller that was shoved into his hands.
They died multiple times, Sam somehow managing to carry Castiel through three waves of zombie attacks. He never understood why Sam would like a game that was so gory.
“With how much you’re over here, I thought you’d get better at this game,” Sam said, eyes still locked on the TV screen.
“Well, we only usually play for thirty minutes or so,” Castiel shrugged. “I don’t have time to play these things at home.”
“Sounds boring,” Sam smiled, a mischievous grin. “That’s probably why you come over so much, other than hanging out with Dean, obviously.”
Castiel shot Sam a look and Sam looked back.
“Dean’s been a bad influence on you,” Castiel managed to say.
“I’m stating the obvious, c’mon.”
Castiel scoffed. “What about you and Jessica then?”
“That’s different!” Sam defended.
Sam and Jessica had the exact same ‘not-relationship relationship’ that Castiel and Dean seemed to be having. The poor kid was obviously head over heels, Jessica was oblivious to it all.
“It’s not.”
“Yes, it is-”
The front door opened, the sound of it closing and keys being tossed into a bowl followed. Dean walked to the living room, he was covered in sweat and grease from his hours at the local burger joint. He looked at the TV and then locked eyes with Castiel.
“Ugh, we were winning too,” Sam sighed, leaning back into the couch. “Fine, Cas, you can go with your boyfriend.”
“Not funny, Sammy,” Dean said, laughing a bit. He awkwardly coughed, gesturing to Castiel to follow him to his room. “I got something to show you.”
Castiel nodded, he placed down the controller beside Sam on the couch and stood up. He started to stare at Dean from behind, the boy was shaking the closer they got to Dean’s room. He was worried Dean got injured at work, which was not uncommon when Dean could be clumsy if he didn’t care enough. Castiel prepared himself to get the first aid kit that Dean secretly kept in his bathroom drawer.
Dean was an idiot sometimes. The first time he asked Castiel to help patch him up, he was a nervous wreck. Castiel was more than happy to help, since Dean used to get into fights at school pretty frequently. Besides, Castiel was trained, first aid and CPR looked great on a resume, so he knew all the basics. After a while, it became a normal thing for Castiel to bandage Dean up in his room, away from Sam and Ms. Winchester freaking out about it.
Castiel looked around, Dean’s room was always messy. It did look quite aesthetic, straight out of one of those corny high school drama movies Dean would make him watch. Tons of old movie posters across the walls, action figures on shelves that were cleaned from dust weekly, even his clothes managed to be scattered in the right places. Compared to Castiel’s bland room, being in Dean’s room was always a nice change, the dim orange lighting filled the dark bedroom with a cozy feeling that Castiel could only describe when Dean was present.
“So…” Dean started but he closed his mouth before anything else could come out.
“So…?” Castiel repeated.
Dean was standing awkwardly on the other side of the room, near his desk, which was covered in paper. There was a board on top of everything, some scribbled writing that Castiel couldn’t make out from how far he was standing.
“You’re not injured, are you?” Castiel raised an eyebrow. “I can go get the first aid kit,” He turned around but Dean’s shouting stopped him.
“No! Wait! Cas, hold on,” Dean tried to collect himself, running his hand through his hair multiple times. “I should have probably waited until I was less sweaty, but I don’t think I can hold it in any longer.”
“What do you mean?” Castiel asked, tilting his head, now he was actually confused. “I can wait, it’s okay, Dean. I don’t mind.”
“I mind!” Dean exclaimed. “I really mind.”
“Are you sure you’re fine? You’re worrying me,” Castiel stepped closer. He narrowed his eyes, inspecting Dean’s face.
“I- Uh… Shit,” Dean sighed, his head tilting downwards to stare at the floor. “I’m so bad at this.”
“Do I need to get Sam? Or Bobby?”
“No! It’s okay, this is good,” Dean grabbed Castiel’s wrist, stopping him entirely. “Just us is good.”
Dean turned his torso around, lifting up the board Castiel saw earlier. The words “CAS, WILL U GO 2 PROM WITH ME?” in big blue marker with hearts surrounding it. There was even a small doodle of Sam in the corner giving an endorsement.
Castiel’s eyes went wide.
Once Dean realized Castiel read everything, he put the sign back down behind him, letting go of Castiel’s wrist and grabbed something from under his bed. A huge bouquet of roses with some poorly crafted paper bees attached in the little gaps.
Castiel didn’t know what to say.
Dean started shaking more, he dropped the bouquet. “Okay, no flowers, don’t worry!” He said, definitely not keeping it together. He pulled out another gift from under the bed, a silver necklace with a silver feather as the charm, similar to the one on his phone charm.
“Dean…” Castiel said, quiet.
“Um… No necklace either? Okay, wait, I got-”
“Dean!” Castiel shouted, stopping him.
Dean stood up slowly, carefully leveling himself with Castiel and stared at him. The two locked eyes, Castiel always noticed the green sparks in Dean’s eyes, they were one of the many things he loved about the boy.
He took one deep breath. “I would… Love to go to prom with you,” Castiel whispered, barely managing to get the words out from how fast his heart was beating.
“Cool… Cool,” Dean nodded, he looked down at Castiel’s lips. Though, his usual coping mechanism of being unable to take anything seriously managed to slip through. “So, was it the flowers or necklace that sealed the deal?”
“You really annoy me sometimes,” Castiel scoffed. His eyes softened, looking at how Dean was a nervous wreck over asking him to prom of all things. “It was you.”
Dean’s mouth slowly turned into a small smile. A comfortable silence filled the room, Castiel enjoying Dean’s body heat before Dean slowly inched closer and closer to Castiel’s face, staring right down at his lips.
Castiel pulled back just before they actually kissed. “How about we save that for the dance?”
“Cas, are you serious?” Dean said, betrayed. His hand moved up Castiel’s arm, gently touching the edge of the overcoat. He lightly grasped the coat, as if Castiel would even think about walking away now.
“I am,” Castiel shrugged, slightly smirking.
“Have you always cared about theatrics?” Dean laughed, letting his head fall into Castiel’s shoulder.
“I’ve waited this long for you to ask me out,” Castiel replied. “I deserve a chance to make it as dramatic as I want.”
“Has anyone ever told you that you’re the worst?” Dean mumbled into his coat. “Because you are the worst.”
“I’m thinking on the dance floor, in front of everyone with the lights flashing,” Castiel added, moving his other hand to hold onto Dean’s. “Or maybe on the drive home? In the Impala?”
Dean perked up at that, he lifted his head up to look at Castiel in the eyes again. “You know what, maybe waiting isn’t such a bad idea.”
Castiel laughed softly, having another staring contest with Dean before lifting himself up by the tippy toes to kiss him on the cheek.