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Castiel was knee deep in Hawaiian wedding plans, his head swimming in flight details, when Dean asked the question.
“What the hell are you talking about?” he asked tiredly. Castiel had only seen Dean a few times during the years his best friend, Jessica, had been dating Dean’s brother, Sam. It wasn't until he was made Jessica’s “Man” of honor that he'd been forced to spend more and more time with the gruff mechanic. Currently they were in Castiel and Jessica’s apartment; he was sitting at his desk surrounded by notes and Dean was pacing around behind him.
“I mean, we’ll already be there, it's not like it would be out of the way.”
“So, you want to spend an extra four days on the island, just you and me?” Castiel asked to clarify.
“Yeah, I mean, you're cool, it'll be cheaper to split the hotel room… think of it like a, a homiemoon . Bros only.”
“Are you high?” Castiel asked, staring at Dean utterly perplexed. Dean wrinkled his brow like he was actually thinking about it, and Castiel shook his head. “Dean, I don't know-”
“Come on, Cas,” Dean insisted.
“My name is Castiel.”
“And I've told you that's a damn mouthful,” Dean scoffed. He paused in his pacing to take a deep breath. “Look, my best friends have all gotten married, and now my baby brother. I just want something for myself for once.” Castiel doesn't know him all that well just yet, but the tiredness in Dean’s shoulders speaks to the truth.
“I'll look into it,” Castiel sighed heavily. Dean immediately brightened up.
“Thanks, Cas...tiel,” Dean said with a sheepish smile.
A couple months later Castiel finds himself walking into the hotel room Dean had been using for the wedding trip. Jess and Sam’s wedding was beautiful, if a bit unconventional, and damn near perfect. The reception after also went off without a hitch; Dean had delivered the usual best man speech with all the expected leering comments and poorly disguised sentiment, and Castiel had given a small speech as well.
The only thing that had put a damper on Castiel’s day was the first dances, when the wedding party joined the bride and groom. It had been arranged that Castiel would be dancing with Dean and Sam’s adopted sister Jo, and Dean would be dancing with Charlie, he and Jess’ friend. Dean had instead grabbed hold of Castiel and started leading him around the dance floor, and while he had laughed it off at the time, Castiel had made sure he avoided Dean the rest of the night.
Now he was stuck in a hotel room with him for the next four days on this stupid homiemoon Dean had thought up.
“Cas, I said sorry. It was just a bit of fun,” Dean apologized again.
“My name is Castiel,” he grunted, dropping his things on the unused bed and sitting down with his back to Dean. He wasn't even sure why he was so upset by the whole thing, he just... was. They went to bed shortly after without saying another word to each other.
They spent the following day sulking on opposite sides of the hotel, bumping into each other when they went back to the room to change for dinner, which coincidentally they were eating in the same place. Castiel swallowed his pride and maintained a level of civility with Dean throughout their meal. By dessert, Dean’s natural charm, and maybe a few drinks, won him over; by the time they were on their way back to the room things were friendly between them again.
They spent the second day out exploring the island, hiking up a dormant volcano and spending time at the beach. Castiel even allowed Dean to help him apply sunscreen to his back, and to his surprise Dean did so without too many inappropriate comments. It was even kind of nice, Dean’s hands practically massaging his back as he rubbed the lotion into his skin. That night, they stayed up late talking, and Castiel found himself surprised again by the depth of Dean’s conversation. Dean played it off well, but underneath his carefree attitude, Castiel was starting to find he was a lot smarter than he let on, and, as Castiel teased, “not quite as emotionally constipated” as he pretended to be.
It was raining on the third day, the kind that no umbrella or poncho could stop from getting you soaking wet. Instead of being discouraged, Dean pulled a portable DVD player and some movies from his suitcase with a flourish.
“I thought Sam was kidding when he said you never go anywhere without your movies,” Castiel laughed, and Dean shrugged.
“What? This is vacation it's a legitimate reason!” Dean muttered indignantly.
They ordered in pizza and watched Fight Club and Pulp Fiction, (because everyone has to see those movies at least once, according to Dean) lounging on Dean’s bed with the DVD player between them. Castiel was asking questions about the movies, and Dean pretended to be annoyed but he was so enthusiastic in his answers Castiel kept on asking just to see him smile.
Castiel woke up, not having realized he'd fallen asleep. The DVD player had been moved, and a blanket draped over him, but he was still in Dean’s bed, Dean laying next to him sleeping soundly.
Closer than next to him. In his sleep Castiel had rolled half onto Dean, his arm flung across his chest. He went to move, but stopped when he looked up at Dean’s face. He'd gained a couple new freckles from their time in Hawaii, his slightly sunburned cheeks rosy with sleep. Dean really was attractive, a softer edge to the masculine cut of his jaw, something Castiel had avoided noticing because of the pressure of the wedding. Now, being so close to him, it was impossible not to notice. So Castiel didn't move, except to maybe squeeze a little tighter as he drifted off to sleep again.
On the fourth day, something had changed. Waking up with Dean wrapped around him like an octopus had probably been the catalyst. As was Castiel’s subsequent freak out and retreat to the bathroom. They were tiptoeing around mentioning it, avoiding talking about this... thing , whatever it was. Castiel spent breakfast in a daze, making polite conversation with Dean about nothing in particular, sipping slowly at his coffee and trying not fidget too much as they slip into silence.
Dean finally breaks the tension on their walk back to the room.
“I wouldn't want to get married out here,” he announced, frowning at the swaying palm trees like they'd offended him.
“Why not? It's beautiful, romantic. The weather’s wonderful,” Castiel pointed out.
“I dunno,” Dean shrugged, “I just...I would want it to be somewhere that meant something to me. Not some far off place.” Castiel glanced at Dean out of the corner of his eye, a bit surprised at the thoughtful look on his face.
“I’d imagine you’d want a smaller crowd than who was here for Sam’s wedding,” Castiel added.
“I’ve never been big on crowds,” Dean agreed. “I’d just want my family there, you know.”
“That makes sense.” Castiel stooped to pick up a pink shell off the sidewalk, tucking it in his pocket for his niece, Claire. “Comfort food for the reception,” he added. “Beer over wine.”
“Of course,” Dean laughed. “But I’ll break out the whiskey for the ones who really want to party.” He winked at Castiel and nudged him with his elbow, and Castiel found himself grinning back.
“Careful you don’t get too drunk, don’t want to ruin that wedding night,” Castiel chuckled. To his surprise, Dean flushed red and looked away, out across the pool as they passed by.
“Yeah...if I ever get there,” Dean sighed. Castiel stopped walking. The final puzzle piece of Dean’s personality fell into place: his self doubt. Castiel didn’t know why Dean felt it, or when it started, but he really wanted to find out, because he wanted to change Dean’s mind. Just in the last three days Castiel had seen enough to know it was unwarranted. Dean had taken a few more steps before noticing his companion had stopped, and he turned back to face Castiel again. “What? Don’t look at me like that!” Dean huffed, crossing his arms over his chest.
“Like what?” Castiel asked.
“Like you feel sorry for me!” Dean snapped. “I wasn’t being all self-pitying and shit, cool it with the puppy eyes.” Dean turned and walked a couple more steps, but when Castiel didn’t follow, he groaned his frustration to the sky. “Forget I said anything,” he groused.
“Dean, if my opinion matters at all, I believe you’ll get there one day,” Castiel said quietly.
“You volunteering?” Dean quipped sarcastically. Castiel didn't say anything. Dean just stared at him for a moment, his sarcastic frown fading into surprise, before flushing and turning away from Castiel with a casual wave. “Okay, Cas, don't get all touchy feely on me,” he chuckled awkwardly.
“My name is-”
“ Castiel, I know,” Dean laughed. “But you know what, Imma call you Cas anyway, because it's short and sweet, like you.”
“I am not short-” Castiel started to protest before he caught up to Dean’s flirtation and his smug smile, and he broke out into a grin.
Okay, maybe he could deal with a nickname.
They find a casual bar for dinner, burgers and fries with a couple beers, and it's like the whole awkward morning and the conversation were forgotten. So what if Castiel got a little lost in Dean’s eyes? So what if he “accidentally” nudged his foot under the table a few times?
So what if, by the time they're packing in the room, Castiel has most definitely realized he has a childish crush on this man that his adult brain refuses to ignore.
Dean’s brushing his teeth, humming some song to himself as he does so, and Castiel is sitting up in bed, pretending to read a book when in reality he's mentally kicking himself for this romcom scenario he's found himself in. Dean climbs into his bed, and Castiel can feel his eyes on him.
“Is there something you wanted?” he sighed.
“Well, there's a lot of things I want,” Dean chuckled, “but I was wondering...am I being presumptuous in thinking there's something going on? Like, between us?” Castiel felt his cheeks heat up and slowly closed his book.
“I feel like you just looked up the word of the day on some dictionary app,” he joked to cover his discomfort.
“Shut up,” Dean grunted, “I read sometimes.”
“Hmmm,” Castiel hummed in disbelief. Castiel shifted onto his side to face Dean fully. “I don't know. Think it's just the close quarters playing with us?” Castiel knows it's not true the moment he says it but he has to say it, to voice that little part of him that hopes nothing is going on so that nothing has to change.
“Maybe,” Dean shrugged, rolling onto his back, sounding and looking disappointed. Castiel turns the light off, plunging the room into darkness. Castiel found himself restless, tossing and turning in thought.
Would it really be a bad thing, trying this with Dean? Castiel had spent more time as Jessica’s third wheel over the years than he had dating anyone himself, he wasn't exactly practiced. The way Dean was acting, blushing and flirting, he was interested, and honestly, so was Castiel. But could they-
“Stop thinking too much,” Dean sighed from across the room. “Get over here.” Cas blushed, but pushed himself out of bed all the same, crawling into Dean’s waiting arms with a smile.
“How was the homiemoon?” Jessica was teasing as they stood at the gate in the airport. Dean and Sam had wandered off to find them some coffee a while back, leaving Castiel and Jessica to catch up.
“It was surprisingly fun,” Castiel admitted with a light blush. Jes sat up in interest.
“Fun, huh. Why are you blushing, Castiel?”
“Because… I think Dean is my boyfriend now,” he admitted sheepishly.
“Details!” she squealed, grabbing hold of Castiel’s arm excitedly.
“I don't have any juicy details, we haven't even kissed yet. I just,” Castiel shrugged, “I don't know, it just kinda...happened.”
“How innocent are you?” she giggled. “You haven't even kissed yet?”
“Shut up,” Castiel muttered, blushing furiously.
“Okay, what did we miss?” Dean asked, walking up and handing Castiel a coffee.
“Oh, Castiel was just telling me how much of a gentleman you were last night,” Jess said offhandedly. Sam almost spilled his coffee.
“Dude, what?!” he sputtered, looking between Dean and Castiel. “Dean, when were you going to tell me?!”
“Eventually,” Dean shrugged, taking a sip of his coffee after winking at Castiel. Castiel smiled, trying not to spill his coffee when Sam clapped him on the back.
“Welcome to the family, Castiel,” Sam laughed.
“Hang on, aren't you jumping the gun a bit-” Dean stammered nervously. Castiel grinned at Sam.
“Call me Cas,” he insisted.
Dean stole their first kiss as they boarded the plane.
“Guess we’re officially official, Castiel, ” Dean hummed as they walked along behind Sam and Jess. Cas snagged their second kiss just before climbing on the plane.
“Guess we are,” he agreed fondly.
A few years later, when it came time for their wedding, they kept to their original plans: burgers and beer in Sam and Jess’ backyard, surrounded by their family.
Of course, they returned to Hawaii for their honeymoon.