It's been three days and Sam hasn't called.

He's really trying not to be a girl about this, but this is the longest he hasn't talked to Sam for at least a year… and, yeah, he counts the two weeks after the bank robbery as the worst point in his life, rivalled only by that week after their Dad died and Dean had to uproot and change everything (not that having a guy he'd never met before die in his arms was worse than his Dad dying, but the timing of everything tipped that over to the worst), but at least then he had Sam to sham being okay for. He was still most off the rails when Sam had gone missing.

"Distract me,"

Castiel should tell him to fuck off. He's sure Castiel is plenty busy and has better things to do than babysit and angsty Dean, particularly given that Cas has been in his company pretty much continually for the past three days. Cas was privy to Dean calling Crowley (and going straight to voicemail, because Crowley is a superior bastard who somehow cuts through Dean's give-em-hell attitude and makes him feel wrong footed without even answering the damn phone) and Dean calling Missouri and making an appointment for next week. Cas has had the extreme delight of listening to Dean flirt with Pamela down the phone for thirty minutes, only to have her screw at Dean for being an idiot and hanging up. He then got Cas to drive him to the diner, because – as he said – his charm works much better when Pamela's reminded of his 'sweet ass' or whatever.

Anyway, it sort of worked, but Pamela isn't happy about it… and it's awkward as fuck making sex jokes when Cas is waiting outside in the car. Plus, Cas has made him attend all his classes (and Dean can't really complain, because if it wasn't for Cas he'd be rotting alone in his apartment, but it's still a pain in the ass) and is forcing him to study by ditching him at the library whilst he goes to his own classes.

First day, he just assed around trying to hit on the librarian… but Cas' expression when he came back to find all Dean had managed to achieve in those two hours was to get Audrey to write her number on his sling. The next day he got her to bring some of the books he was supposed to read six months ago, which he probably could have reached himself with his left handed, but the girl obviously wanted to be useful. Anyway, Cas had looked far too pleased, so the next day he actually tried reading them… which was progress.

"I don't know how I'm supposed to distract you, Dean."

"Oh come on," Dean complains, "It's not complicated, Cas. Tell me all about your family rebellion. So, you finally had enough of their religious differences and Michael being a dick, you jump ship… move to Kansas, of all places, and then what? Build up a liver of steal and sleep around a bit?"

"No,"

"No to which bit," Dean says, pulling out his cigarettes with his left hand and going through the significantly more difficult of lighting up without his right. He's not technically allowed to smoke in the apartment and, yeah, he wouldn't if there was a chance Sam would be here… but, that's not looking very likely. "Because, Cas, I've seen you take Tequila like a boss, and that's gotta have taken a lot of drinking."

Cas looks disapprovingly at his cigarette but doesn't comment.

"I'm guessing you didn't take up smoking."

"No," Cas says, "And you shouldn't have done, either."

"I needed it," Dean says, and he's not lying, "you can't win every battle. So, sleeping around?" Cas looks somewhat uncomfortable. Dean sits up straighter and raises an eyebrow at him, because… I mean, come on. Who breaks free of a family that is 'controlling' and 'strict' and doesn't fucking rebel? "Oh come on, what kind of nerdy angel are you?"

Cas has become completely still.

"Shit, please don't tell me you're a virgin," Dean says, because yeah, there's not a chance in fuck that his only friend that isn't really family could be a virgin. That shit's just not right.

"No,"

"Right, good," Dean says, stubbing out his cigarette in his make shift ashtray with a grimace, "not that… well, how many people are we talking?"

He's half curious because he's told Cas a lot about his life at this point, but this isn't something that's ever come up before. He'd pretty much filled in the gaps between Cas moving to Kansas and Cas meeting Dean with lots of rebelling and sex and alcohol and whatnot, just because he's pretty sure that's what ninety percent of the population would do in his shoes. Then again, this is Cas… and now he's thinking about it, his brain is short circuiting instead of placing Cas in any of those situations.

"One… person," Cas says, and Dean's glad he already put out his cigarette because frigging hell.

"That's almost as bad," Dean says, "How?"

"We're not all like you, Dean."

"Yeah," Dean says, "I get that, but one person? Cas, that's a frigging tragedy. You know what, we're going out."

"What?"

"We're going to go out and we're gonna hook you up," Dean says, decisively.

One person means Cas must have been seriously hung up on the girl, because no one discovers sex and then puts it back on the shelf for years unless that one really fucked them up. And, yeah, Dean hasn't been properly hung up on someone from a long time, because Dean doesn't do relationships or fall in love or any of that crap, but it has happened and the one night stands that come afterwards are an important step in getting it out of your system. Sort of.

He is technically helping Cas out with his finances, lest Michael cuts him off from the big bank account tomorrow (which Cas had assured him is a very real possibility), which is how he wound up broke and asking Ellen for a job, anyway. Still, this doesn't feel like a very fair deal on Cas' end… because he's driving him around and keeping him company and is basically spying on Sam for him, when all Dean's done is told him to keep his receipts for the next week so I can get some idea of how Cas is wasting his money.

And this is something he can do.

He can't get Sam to call him or forgive him. The silence from Crowley probably means that he can't do shit about their financial situation (or, else, Crowley is just enjoying letting him stew) and he probably can't pass college or make anything else right, but he can get Cas laid.

Plus, it's an excellent distraction.

Cas is frowning at him.

"It'll be fun," Dean says, standing up and reaching for his jacket, "and you're shit at distractions, man."

ooo

Dean has a hundred percent never seen Cas look so nervous and uncomfortable and out of place, even when Dean buys him a whiskey and tells him to drink up whilst he scopes out the place. It derails Dean so much that he winds up just staring at him instead of looking round for Cas' potentially hook ups, because, yeah, Cas is an odd ball but he never looks this uncomfortable.

He really hopes he hasn't fucked this up, because this is all good intentions and stuff. He doesn't really care that Cas is practically a virgin or whatever, he just needed to be out of the apartment and somewhere else for a bit. He needed something to do.

"What about the girl near the door?"

"Dean," Cas says, his voice quiet and insistent. He's not looking at him. Cas always looks at him. "Dean, I'm gay."

Oh.

Right.

Well, fuck, that sounds about right on the uncomfortable stakes.

"Uh, well, I probably can't help you then," Dean says, feeling equally uncomfortable round about now. Cas does turn to look at him, now, the edge of something terrifying in his blue eyes. "I don't know crap about pulling dudes."

Cas relaxes slightly.

"I apologise," His voice is all deep and formal and reserved.

"Don't," Dean says, because he's not sure what exactly Cas is apologising for but he doesn't think he needs to apologise for anything at all, and he wants to skip from this moment to more comfortable territory because fuck this conversation is bordering on an emotional talk Dean feels they should have, but he hates that crap. "Two doubles,"

His brain is catching up past the awkwardness (which is difficult, because the awkward is suffocating him) and focusing on their conversation about Cas' family. It's seeming like Michael is a homophobic douche bag, and Dean has a renewed desire to punch him in the face. Jesus.

"You could have just told me, Cas," Dean says, as the bartender brings their drinks. He's thinking of Cas' uncomfortable silence in the drive here, which means Cas was already going over this conversation in his head; he wonders what Cas thought he was going to do and feels like a dick. He honest to God didn't mean to assume things, and… Cas should know he doesn't give a fuck. "So, this one person…" Dean says, filling in 'dude' in his head, because yeah Cas hadn't specified, "he was your boyfriend?"

He's not a sixteen year old girl, so he doesn't really want to have the losing virginity conversation, but it's not sure what he needs to say to make Cas realise he doesn't care that Cas is gay now he's already gone and fucked the whole thing up.

"Yes,"

"Figures," Dean says, "you're definitely the type to lose it in some classy way."

"Being in a relationship doesn't immediately qualify it as Classy, Dean,"

"Wouldn't know," Dean grins.

"Why am I not surprised?"

"You calling me a whore, Cas?" Cas just raises his eyebrows slightly and Dean can feel himself laughing without really meaning to, because Cas is just too fucking perfect. "Well, whatever, I'm pretty sure you outclass me on that front," Dean says, glancing down at his scotch.

He's pretty sure he was fifteen, the girl was called Emily and that they skipped town later that day, before he had a chance to mention to her that he was leaving. It was at a motel, in the middle of the day, whilst Sam was at school and his Dad was off breaking the law somewhere… so, yeah, neither remarkable or special and definitely not classy. It probably also classifies as one of his more successful relationship type things, which is pretty depressing now that he thinks about it.

"So, what did the dick do?"

"I don't want to talk about it," Cas says, finishing his double with a clinical smile.

"Yeah," Dean says, "I figured. No one just sleeps with one person unless they're still seriously hung up on whoever that person was."

"Not anymore," Cas says, glancing up at him. He feels better now they've got the eye contact thing sorted again. Cas sort of invades his personal space on a day to day basis, and he definitely oversteps the line of when it's acceptable to stare at anyone, but it's not like Dean looks away and takes a step back – it definitely feels more normal now Cas is back to staring at him.

"Good," Dean says, clapping a hand on Cas' shoulder, "he probably wasn't worth it. So, huh… this what you meant about Michael not accepting you." Cas winces. "Sorry, man, but I gotta ask."

"Yes."

"What a bag of dicks," Dean mutters, angrily, "I'm so over feeling sorry for that douche, Jesus." Cas smiles. "If I ever meet him, I swear I'm sending him straight to hell."

"That's not necessary,"

"I hope for your sake it isn't," Dean says, "you're well shot of that dick."

"He's my family," Castiel frowns.

"No, he aint," Dean says, "I know things about family, Cas. And maybe mine belongs on an afterschool special, but none of us would do that to each other. Okay?"

"In which case, I seem to have no family at all."

"Maybe you should find Gabriel and Anna," Dean says, quietly, because he's been thinking about a lot since Cas mentioned it. Especially with this new information about Michael, it seems like maybe he's been irrationally hating the wrong family members.

Maybe, sometimes there's a good excuse for leaving.

"Enough with this chick flick," Dean grumbles, because getting out the flat was supposed to make things lighter and easier and instead they've gotten stuck in a heavy conversation about family and sexuality and, yeah, that really wasn't his intention. "You good?"

"Yes," Cas says, "I'm good." He sounds kind of amused which is a big up from dejected, but probably not what Dean was aiming for.

"Hey, Cas," Dean says, pushing back his chair, "how's about, if I beat you at pool, you gotta give me a lift home?"

"You're wearing a sling, Dean."

"Yeah," Dean grins, "and you haven't got a chance in hell of winning."

ooo

Cas is slightly better at pool than previously expected and Dean is probably as arrogant as could have been predicted, because Cas does win and they wind up having a big debate about what Dean now owes Cas, given they never specified.

Cas wants Dean to promise to congregate a load of conditional verbs, which is the geekiest request Dean has ever received… and Dean wants to call the difference another drink and be done, because he's so frigging fed up French (and he's not failing, which means there's no point getting any better).

And then the girl that Dean had vaguely considering hooking Cas up with, before the whole awkward coming out conversation, has caught his eye and appears to be heading in their direction.

He's about to turn to Cas and say something about how his sling is a frigging chick magnet and how that makes zero sense, because how good can it be when he's incapacitated by his sling. And yeah, there's probably a way around it, but it'd be awkward and probably painful and annoying and it's definitely not much of a turn on, but whatever.

Cas, however, has noticed their arrival and looks pretty damn terrified at their approach… which is strange, cause Cas isn't scared of Ellen (or Jo) whilst Dean most definitely is, but his thought is cut off by the girl introducing herself.

She's called Trish and she's a waitress stroke aspiring actress and it takes all of two minutes before she's managed to pull him away from Cas enough that Dean can't hear their conversation. Dean turns around to make sure Cas is okay, because the guy looked pretty spooked… then stops short.

The other girl, whose name he didn't get, is way up in Cas' personal space and Dean's not entirely sure what he should do.

"Your friend okay?" Trish asks, and Dean isn't really sure what the answer to that is, because he can't get a read on Cas' expression thanks to the girl. She moves slightly and Cas' eyes lock on Dean, and their panicked and unsure and yep clearly Cas can't handle very forward advances and –

Cas says something that Dean can't hear. The girl takes a sudden step backwards, Dean makes a move to rescue Cas, when the girl slaps him round the face.

"Oh my God," Trish says, rounding on him just as her friend bursts into tears.

Crap.

"Cas," Dean mutters, grabbing hold of a handful of Trench coat and pulling him towards the doorway because he's pretty sure that they've just managed to gain two very pissed off women and a whole lot of attention from the other people in the bar. "Cas," Dean grins, when they're outside, "what the hell did you say?"

"I don't know," Cas says, eyes still wide and panicked.

Dean bursts out laughing.

Then he can't stop. He's reached out to hold onto Cas' shoulder with his good arm and there's a sudden light feeling in his chest, like he just dislodged something. It's been a long time since he laughed like this and it's been a long time since he's had a few drinks for fun and not because he's trying to distract himself, or sleep, or just numb the feeling (or lack of feeling) that occasionally threatens to eat him from the inside out. He certainly hasn't had this amount of fun with his brother for an age, because he's the responsible guardian and that's kind of shitty because he wants Sam to be his best friend.

"Never change, Cas," Dean says, still grinning, as the panicked expression on Cas' face drops slightly. He'd quite like to stand and absorb this moment for a while – because he hasn't felt this okay in an absolute age, and all it took was Cas accidentally upsetting some random girl – but Trish standing in the doorway pointing them out to the bartender who served them earlier, so it's almost definitely time to leave. "Time to go," Dean says, pushing Cas towards the car.

"Ah, man," Dean says, once they've pulled out the parking lot and are well on the way to Cas dropping him off at his apartment (which is irritating despite his good mood because, seriously, he's not a fifteen year old girl and Cas' car sucks), "it's been a long time since I ran out of a bar like that." Cas gives him a maybe you should have run out of a bar last week, instead of getting in a fight look, which Dean suspects is probably fair but a real mood killer. "I think you're a bad influence on me."

Cas laughs at that.

"Don't let your brother know," Cas says, "he'll get someone else to babysit you."

"I haven't had that much fun with Sammy in years," Dean says. It was meant to be a light comment but it came out more like a confession, because he doesn't want it to be like that. Sam is supposed to be everything and admitting that, yeah, his brother is a damn pain in the neck and he hasn't properly enjoyed his company for ages is painful.

It shouldn't be like that.

"It would help if you weren't constantly worried about him," Cas says, "but I suspect most brothers have more fun with their friends."

"Yeah," Dean says, "well, we're not exactly most people."

"No," Cas agrees, "I enjoyed myself too, Dean."

"Even getting slapped in the face?" Dean asks, grinning again because Cas' face had been frigging precious. Cas' expression turns a little smitey and Dean leans back in the passenger seat with a grin, before he remembers that Sam's gone and Dean can't afford jack shit.

Dean frowns out of the window for the rest of the ride home, but he doesn't have another drink when he gets home and it only takes him forty minutes to get to sleep…. So he's counting that as a big improvement.

And maybe Sam will call tomorrow.