(Requested by the amazing @jtblabfactory. <3 Enjoy!)
Most people who knew Dean wouldn’t describe him as a shy person. There was a reason for this: in general, Dean was very careful to only place himself in situations with which he felt familiar and in control.
This involved talking to women, for one thing. Women, he could handle. He felt comfortable with his attraction to them, for one thing, and he’d seen from other men (the ones on TV, as well as his father and male friends) how flirtation with women typically worked.
Men – now that was another matter entirely. For one thing, Dean had never fully accepted his attraction to men. With particular mortification, he recalled being in middle school and trying to convince himself he wasn’t gay by promising himself he would “only be gay at night.” Of course, now Dean knew that he was actually bisexual, but that was besides the point.
For another thing, Dean knew his father wasn’t entirely comfortable with same sex relationships. Dean had listened to him use the word “gay” (or sometimes worse) as a synonym for “bad” or “lame” without even thinking about it. Of course, if questioned, he would deny that he had anything against queer people, but that fact only served to confuse Dean further.
And so, one way or another, Dean had grown up to miraculously morph from a suave, charismatic charmer into a clumsy, shy, tongue-tied oaf whenever an attractive man was in the room.
He recalled walking into a table when his friend Aaron had flirted with him (and unlike Aaron, Dean didn’t even have the excuse of being drunk). The disastrous Freudian slip he had made with his Freshman psychology professor. All the times guys had flirted and winked at him and all he could do was sit there and stare, or babble something garbled and unintelligible.
This was generally something Dean could live with. He never had any trouble finding FEMALE partners, and least, and they kept him satiated for the most part. But every so often, Dean met a guy he REALLY liked, one he would have loved to get to know better, one he would have loved to talk with and laugh with and really get to know, but couldn’t.
Such was the case with Castiel Novak.
The worst part of this might have been the fact that he came absolutely out of nowhere. Dean hadn’t been expecting meeting a potential partner that evening – for once, that was the furthest thing from his mind. He’d been planning a (relatively) quiet evening out, unwinding with his friends before finals week.
At present, the small trio – consisting of Dean, Charlie, and Kevin – sat at their usual table at Harvelle’s Roadhouse, listening to Charlie recount one of her elaborate sexual escapades (involving multiple female partners and some elaborate Star Wars role play) with a mixture of horror and fascination.
“…And if we ever do slave-Leia role play again, that was the LAST time I’ll be Jabba!” she finished, leaning back with a degree of smug satisfaction at the stunned expressions on her companions’ faces.
“Well,” said Dean, clearing his throat. “That was, uh…”
“Has anyone seen Sam?” Kevin blurted, not wanting to linger on the subject any more than he needed to.
Dean retrieved his phone, glancing at their latest text conversation.
“Last I heard from him, he said he’d be here in fifteen minutes.”
“Wasn’t that, like, fifteen minutes ago?” Charlie pointed out.
“Well, yeah,” Dean shrugged. “But you know Sam. All those extensive women’s hair treatments can take a while.”
Sam had been accepted in Stamford two years after Dean. He was still currently in his freshman year while Dean was a sophomore, but several of Sam’s professors had mentioned that due to his exceptional academic performance, he might be able to graduate early.
Dean was…well, he wasn’t exactly less intelligent than Sam. Dean was actually surprisingly bright. He was just absolutely terrible at applying himself.
Glancing impatiently at the clock, Dean was just about to text Sam again – at this point, he’d had a fairly rough day, and was very eager to get some liquor and at least two cheeseburgers into his system – when a familiar voice said, “Sorry I’m late, guys.”
Dean turned out, irritably, and said something along the lines of, “Well it’s about goddamn – oh, SHIT.”
Sam was here alright, but he was not alone. Standing to his right was possibly the prettiest man Dean had ever seen.
His eyes were a striking cerulean blue, wide and ponderous, and his hair was a disheveled mess of black, sticking up in all directions like he’d just rolled out of bed. Dean’s eyes wandered down his full, chapped lips and redundancy of stubble to his unfortunately…EXCESSIVE attire: whoever Sam’s companion was, he was currently wearing approximately seventeen layers of ill-fitting clothes, including an old-fashioned, slightly rumpled trench coat, a black suit, and a necktie that was not only extremely crooked, but also on backwards.
After a presumably uncomfortable silence – for which Dean was, thank God, not mentally present – Sam said, “Well jeez, it’s good to see you too, Dean.” He gestured polightly to the young man to his right. “Charlie, Kevin, I think you’ve met my friend, Cas. Cas, this is my brother, Dean. Dean, this is Castiel.”
“Um, hi,” Dean mumbled, awkwardly trying to avoid eye contact.
“Hello, Dean,” Castiel grumbled, his voice deep and gravelly beyond his years. He said the word “Dean” like he’d known him all his life.
*Well,* Dean thought, already feeling like he was about to faint, *So much for relaxing this evening.*
Castiel had had a long and stressful week. Well, as a pre-med student who was also working a full-time job, most weeks for him generally WERE long and stressful.
It wasn’t so much that he disliked dissecting adult pigs, provided the animal had been properly comforted before its slaughter, but after doing it at least six times this semester, it had grown tedious even for him.
Normally, Castiel loathed any kind of social gatherings, or anything that involved talking to people. He’d much rather be home with his books and his cats and a lot of peanut butter and jelly sandwiches.
But tonight, he had made an exception. Because of Dean Winchester.
Castiel had tutored Sam in chemistry the semester before, and slowly but surely, they’d become good friends. Cas was a good listener – he much preferred it to speaking, anyhow – and more than anything else, Sam talked about his amazing older brother, Dean.
He told Castiel about how Dean had saved him from a fire when he was a baby, and he told him how he’d taken care of him as a child, basically becoming his foster parent after their mother died. Dean had worked full time throughout his adolescence, often working multiple jobs at once so Sam wouldn’t have to.
Sam practically worshiped Dean, and from what Castiel had heard, that was completely justified. Dean sounded like a truly great man.
Needless to say, when offered an opportunity to meet the fabled Dean Winchester, Castiel was not going to turn it down.
And Dean certainly didn’t disappoint: He was without a doubt the most gorgeous man Castiel had ever seen, with his golden-blond hair and emerald green eyes and smattering of honey-colored freckles.
And yet, from the moment he and Sam had arrived, Cas already regretted coming. For one thing, Dean appeared to immediately and inexplicably despise him.
From the moment he saw him, Dean had just stared at Castiel for what seemed like an hour, then simply turned away and had refused to look at him since.
Castiel didn’t understand. He knew he was socially awkward, but he had barely said anything, and certainly nothing that could possibly have offended Dean. ‘Hello’ still was the correct term, wasn’t it…?
He wondered if it could be the way he was dressed. People sometimes found that odd. Castiel looked down to examine his attire, and only then did it occur to him that his tie was on backwards. He wondered briefly how long it had been like that and why no one had mentioned it to him.
Oh, well. There was no way to discretely fix it, for the time being. And anyway it certainly didn’t seem like a valid enough reason to dislike someone.
“So, Dean,” Cas said, forcing a smile. “Sam tells me you’re a, uh…business major?”
“Yeah, that’s me,” said Dean flatly, not looking up from the single spot on the table, at which he’d inexplicably been staring for the past ten minutes.
There followed a long silence.
Castiel sensed awkwardness.
“Cas has majors in biology and physics,” Charlie added helpfully. “And a minor in religion. Don’t you, Cas?”
“Yes,” said Castiel, sheepishly. People seemed to get irritated with him when he told them about his majors – it always sounded to them like he was bragging.
Another silence. Castiel tried to think of something else to say, but luckily, the owner of the establishment – Ellen Harvelle, who was apparently a friend of Sam and Dean’s – provided a welcome distraction.
“Can I getcha anything, boys?” she asked, voice thick with Southern drawl.
“Sure, Ellen,” said Sam. “Um, just five beers should be good, to start with.”
“Actually, could I just have orange juice, please?”
Everyone present turned to look at Castiel, bemused expressions on their faces. He got that a lot, but alcoholism ran heavily in his family, and it seemed to get progressively worse with each generation. If he did drink, Castiel might guzzle an entire liquor store in one night, for all he knew.
“Sure, darlin’,” Ellen said, taking it down. Looking to the rest of the party, she added, “Anything else? Something to eat?”
“How ‘bout it, Dean?” Sam suggested hopefully. His tone of voice told Cas that Sam was still hoping to snap Dean out of his funk. “I know you could always go for a burger.”
“I like burgers,” Castiel added uselessly, but it was true. Cas had always had an abnormal amount of fondness for red meat.
“Um, actually…” Dean muttered. “I don’t feel so good. I think I might have to call it a night, you guys.”
Before anyone had a chance to respond, Dean had already stood up. Awkwardly. Knocking over a chair as he did so.
“It was, uh…nice to meet you, Cas,” he muttered, not bothering to look at him. “Hey, I’ll see you guys later.”
Next thing anyone knew, Dean was practically sprinting for the door, leaving his companions sitting in perplexed silence.
“What in heaven’s name is with HIM?” Ellen remarked, finally, gesturing to the direction in which Dean had gone with her thumb. “I’ve never seen him reject FOOD before!”
Sam sighed, leaning back in his chair wearily. “He’s just being Dean, Ellen,” he muttered, as if that explained everything.
Castiel stared forlornly at the floor.
At this moment, he was certain of just one thing, and that was that Dean hated him.
“He HATES me, Sammy!” Dean practically bawled into the phone the next night.
“Dean, just get a hold of yourself. I’ve known Cas for a while now and he’s a real nice guy, nice as they come,” Sam was saying, on the other end. “He likes everybody.” Pause. “Well, except for his literature professor, that, uh, Metatron guy…Cas hated him.”
“And ME, Sammy. He HATES ME,” Dean slurred. “I mean, how could he not!? I’m freakin’ USELESS!”
“…Dean, are you drunk.”
“Dean, you promised me you’d cut back!”
“Yeah, well…” Dean said, taking another swig of the boxed wine he’d been guzzling for most of the evening. “…Guy can’t live on caviar alone, Sammy.”
“Dean, that doesn’t even make any sense,” there was a long, audible sigh on the other end. “Look, Dean. Just, sleep it off. And if you really like Cas-”
“-I’ll set something else up between you guys. Okay?”
“…Yeah, okay, Sammy,” said Dean, with a fair amount of hesitation. As much as he wanted to see Cas again, the thought of repeating that disastrous first encounter was really something he could do without.
“Okay. Now, just…” the exasperation in Sam’s tone was audible. “Get some sleep.”
“Yeah, sure, Sammy, sure.”
“Alright. goodnight, Dean.”
Dean knew that, judging by his present mood, sleep was probably not in the cards. Dr. Sexy M.D. most certainly was, however. As was an extra large pizza with the works, which he had ordered at least an hour ago (in reality, it was only about five minutes, but everything seemed to take longer when Dean was waiting for food).
In the meanwhile, Dean went back to guzzling his liquor and sobbing over Doctor Sexy like some middle-aged, suburban wine mom.
Just as it seemed that Doctor Sexy was going to confess his love for the sexy but aloof Dr. Garcia, there came a knock at the door.
Dean considered ignoring it, when he remembered: the pizza.
“Coming,” he slurred, standing up and WOAH, he was more drunk than he thought he’d been.
Dean stumbled to the front door, pausing along the way to grab a few dollars from the stash underneath the silverware drawer, opened the door, and -
For a very long moment, Dean was certain he was hallucinating.
Standing at the front door, wearing a bright blue uniform and cap that read “Chuck’s Pizza and Subs” (and yes, the trench coat, too), was Castiel. Holding what appeared to be Dean’s extra large pizza.
From the stunned expression on his face, Castiel’s thought process appeared to be roughly the same as his.
After a long moment of awkward staring, Dean slurred loudly, “CASSS?”
“What’r YOU doing here?”
“I, uh,” Castiel shuffled awkwardly. “I assume you ordered a pizza.”
Cas looked at him blankly. “I deliver pizza, Dean. It’s my job.”
“…Right,” Dean mumbled stupidly. “ ‘Course, ‘course.”
Castiel cleared his throat, more nervous than impatient. “Would you like the pizza, or…”
“OH, RIGHT,” Dean blurted, feeling like an idiot. “…Um, how much do I love you?”
GODDAMN IT, FRESHMAN PSYCHOLOGY ALL OVER AGAIN.
“I said, how much do I owe you?” Dean lied.
“Oh, of course,” Cas muttered, blushing furiously. “Uh, eleven seventy-five, please.”
As Dean fumbled to count out the correct amount, fingers trembling (partially from the alcohol and partially from the nervousness), sweating under Castiel’s constant, cerulean stare.
“I wanted to talk to you,” Castiel said bravely. “About the other night…”
OH FUCK, NOT THIS. Dean was far too inebriated to deal with this right now.
“…I don’t know if I upset you in some way, but if so, I’m-”
“KEEP THE CHANGE,” Dean blurted, thrusting two hundred dollar bills into Castiel’s hand.
“I’ll talk to you later, okay? G’night!”
And with that, Dean unceremoniously slammed the door in Castiel’s face.
“Fuck, fuck, fuck…” he muttered, slumping against the door jamb, as breathless as if he had just run a half marathon.
If Castiel didn’t hate him before, he sure as hell did now.
“…Dean?” came a muffled, raspy voice from the other side of the door.
HE WAS STILL OUT THERE!? When would this torture end!?
“Would you still like your pizza?”
*Dean, you asshat,* Dean thought, *YOU FORGOT THE GODDAMN PIZZA.*
“Uh, just leave it out there.”
“…Dean, are you sure?”
“Yeah, I’m sure,” he assured him miserably.
“…Alright.” There was a brief, light shuffling as he set the box down on the sidewalk, and a hesitant, “Good night, Dean,” followed by receding footsteps as Castiel walked away.
Dean waited at least another twenty minutes to make sure he was gone before he dared venture out to retrieve his (now cold) pizza, secure in the knowledge that there wasn’t enough boxed wine in the world to absolve him of his misery.
Dean always was just the slightest bit dramatic.
“Dean, you need a tutor,” Sam had said.
It had been two weeks since Dean’s fateful encounter with pizza man Cas, and he still hadn’t recovered. His mortification over the event remained every bit as strong as it had been directly after the disastrous exchange.
“I do not!” Dean had shot back childishly. “I’m pullin’ an A average in most of my classes!”
“Yeah, but you’re this close to failing history. You don’t want to have to retake it next semester, do you?”
“GOD no,” Dean muttered. He hated his history class, and absolutely despised its teacher, Naomi.
“Then you admit you need a tutor.”
“Dean,” Sam had sighed. “There’s nothing wrong with needing help. Hell, I had a tutor when I was first starting out, and I was straight As in everything.”
Dean grumbled something illegible, looking like a petulant little boy.
“I had someone really amazing, by the way,” he added thoughtfully.
“I think you’d really like him.”
“I think,” Sam had said, looking oddly pleased with himself. “I just might be able to get you the same guy.”
Dean hadn’t put two and two together at the time, but oh, he sorely wished he had.
Up until Sam and the mysterious tutor actually showed up at the front door, Dean had actually been having a great and enjoyable day off. One of the great things of having inherited his father’s house was that Dean didn’t have to deal with any roommates (well, aside from Sam, but he spent most of his time at the library. Nerd.), or any PEOPLE, for that matter: he could just kick back, eat pie with his fingers, and watch reruns of good ol’ Doctor Sexy MD.
And then, just like that disastrous night weeks before, there came a knock at the door.
Still licking pie filling off of his fingers, Dean stretched, reluctantly turned off the television, and walked to the door.
And, standing there, was an infuriatingly smug-looking Sam. With Dean’s new tutor.
You guessed it: Castiel.
From the miserable expression on his face, Castiel didn’t appear to want to be there any more than Dean did. This was entirely the doing of Sam “Matchmaker” Winchester.
“Hello, Dean,” Castiel grumbled unhappily.
The only thing Dean could think to say was, “How many freakin’ jobs do you have!?”
The week – and Castiel’s tutelage – was drawing to a close, and Dean was no more prepared than he’d been before.
This wasn’t Castiel’s fault, obviously. Well, maybe it was, but indirectly. After all he didn’t TRY to make Dean get so lost in his eyes that he couldn’t think, or so distracted by the movements of his lips that he couldn’t concentrate on what he was actually saying.
“…And that concludes our lesson for the evening,” was all Dean picked up on, along with some shit about the Minoans wrestling with bulls and whatnot.
Dean wanted to say something, to thank him for trying to help. He wanted to tell him how amazing he was, but nothing would come out. Nothing but a short, curt, “Right. Thanks.”
Dean carefully avoided eye-contact as he gathered his notebooks, stumbling a bit as he turned to leave. In retrospect, he had no idea where he thought he was going – they were still in DEAN’S house, after all.
“Dean,” Cas grumbled, and Dean paused, tense all over. “I have something I need to tell you.”
“Well, look Cas, I’m really sort of busy so-” Dean mumbled desperately, all in a single breath.
“Please, it will only take a moment.”
Reluctantly, Dean turned around to face his companion. Cas looked amazing like this, without that bulky trench coat, his shirt unbuttoned towards the top, tie loose. And his hair, well – ‘sex hair’ was the only way to really describe it. It was incredibly distracting.
“Dean, I know you don’t…” Cas swallowed. Also incredibly distracting. “I know you aren’t particularly fond of me.”
“Cas-” Dean started to say.
“Dean, please let me finish. I wanted to tell you that I think you’re a truly good man.”
Once again, Dean felt ready to faint. Had most people said this, it would have come off as faint praise, but the way Castiel said it – God, he made it sound like the most amazing thing in the world, like he thought Dean hung the stars or some shit.
“What you did for your brother was truly noble, Dean,” Cas went on. “And I know how you feel about me – I know that I’m inconsiderate, and that I don’t think before I speak, and I’m a poor excuse at what I do. But I would be truly honored if I could be your friend.”
Dean hadn’t the slightest fucking clue what to say. His mind was a jumble of panic and euphoria, through which one thought screamed at him: GET YOUR ASS OUT. NOW.
“I gotta go,” he blurted, like an idiot.
“Dean-” Cas started to say, and in a bit of a panic, grabbed his shoulder.
What followed the best and the worst and the most mortifying moment of all of Dean’s 20 years of life.
Dean’s notebook hit the floor. And it fell open. To a page that was completely and totally packed with countless doodles of tiny hearts, with names like “Castiel Winchester” and “Dean Novak” and “Dean + Cas” inside of them. Towards the bottom right-hand corner was a surprisingly elaborate pen and ink drawing of what appeared to be Castiel’s face.
Cas stared at it for a long, long time, the look of sheer confusion on his face something that would forever remained ingrained in Dean’s mind, while Dean just stood there like a complete moron, face getting redder by the second.
He was honestly expecting Cas to be outraged, to demand an explanation, maybe to threaten lawsuit (obviously, the last one wasn’t realistic, but in his panic, Dean wasn’t quite thinking clearly).
But then, Castiel looked back to Dean – their faces only inches apart now – and all he said was, “Why didn’t you tell me?”
A thought rang very clearly throughout Dean’s head: BECAUSE I WAS SCARED.
But unfortunately, the simple truth was that Dean wasn’t very good at communicating his emotions. So he just sort of muttered, “I dunno.”
They looked at each other for a long, long time, just staring into each other’s eyes like a couple of dumb asses.
“Dean,” Castiel rasped, and Dean was certain his voice was a bit deeper than it usually was. “May I kiss you now?”
This time, there was no hesitation at all.
“HELL yes,” Dean blurted.
And Castiel did. Hard.
Dean had expected to feel shame, like he did the day after his freshman roommate’s mother visited. That had been admittedly regrettable, but Pam had been a very attractive woman for someone her age, and it seemed like a good idea at the time.
But today, all he felt was euphoria.
“You don’t regret last night, do you?”
At present, Dean was walking a very disheveled-looking Castiel to his car, clad in nothing but jeans and one of Dean’s band tee shirts. It was painfully obvious what they’d been doing, if the stares of Dean’s nosy neighbors were any indication.
“Cas, buddy,” Dean grinned, wrapping his arm around his companion’s shoulder. “I feel better than I have in years.”
Castiel looked pleased with this information, at least for the time being.
“Dean?” he said again, after a moment.
“What I did. Was I…correct?”
Dean smirked again. “VERY.”
God, he looked amazing like this. Dean decided this moment should be commemorated or preserved in some way (it might be forever before he saw him without that trench again, after all), and seeing the impala gave him an idea.
“Hey, Cas,” he said. “Get over there by the hood, I wanna try something.”
Castiel looked confused by the request, but complied anyway.
“Yeah, that’s good. Now…open it.”
Dean had seen many girls pose this way, in posters and dirty magazines and in movies, but in his humble opinion, a wanton-looking Cas trumped all of them.
“Hold it right there, that’s perfect.”
“Dean, what are you-”