A/N: A friend of mine recently got stuck in a hospital for a while, and her only highlights of the day where when I would print out fics and bring them to her. Then she started requesting fic from me. The request for this one was a bit… iffy, for me. Suffice to say I edged outside of my comfort zone here, and into uncharted waters for me, and with any luck I didn't completely screw it up.

This is a pretend-multi-chapter fic. It was all one long thing when I wrote it, but I chopped it into pieces before posting this because I'm evil. Also, I'm still in the processing of doing last-stage cleanup. There will be more Cas 'n Dean in chapter two, I promise.

I do love feedback, so if you have a favorite line, quote it and I will has a happy!


Most bad things that happen in the world, as far as Sam is concerned, start with some well-meaning but misguided soul deciding to help out someone in need, often without the knowledge of that someone. This is rapidly turning out to be somewhat similar to one of those times, except for the well-meaning part, and the whole misguided thing. And, of course, the use of the word soul is highly debatable.

Gabriel does these sorts of things for his own entertainment, knowing full well that it most likely won't end well. And, Sam believes, some bizarre ripple in the fabric of reality at the time of Gabriel's birth allowed him to slip into the world without getting saddled by that pesky little soul thing. What he was born with is a salesman's false charm, and the ability to see right through people, and a hangdog expression that is nothing like Sam's own puppy-dog eyes and instead puts one in mind of a mournful old basset hound.

The amazing thing is not Gabriel's determination- when he gets his teeth in a plan, it's hell shaking him loose. The amazing thing is that Sam is listening to him, even considering his idea, if for no other reason than to make him go away that much sooner. He tried you ranting lunatic, get out of my life once, before realizing Gabriel lives in Reverse Psychology Land, and now couldn't get the older man to leave him alone without use of a large box addressed to some small town in Brazil and a tranq gun with a big enough dose to drop a moose.

"Let me see if I've got this right," he says. "You want us to hook up our brothers."

"Yes," Gabriel says in a loud and slow tone typically reserved for particularly dense children, American tourists in foreign countries, and puppies being taught not to piddle on the rug. "You said yourself you're tired of the whole Dean and the Bimbo of the Week routine, and I'm tired of the whole Cas the Involuntary Celibate thing. Two birds, one stone."

There are three chairs in Sam's office. One day, he chooses to believe, one day Gabriel will slip up and sit down in the one with wheels, and Sam will roll him right out the door. And, quite possibly, right down the stairs.

"Does Cas even like guys?" Sam asks. Might as well start poking holes in Gabriel's plan now- Sam hardly knows where to start, since it's already composed almost entirely of holes- before they go ahead with it anyways. The only thing that bothers Sam about Gabriel more than the man himself is how easily he gets Sam to cooperate in his idiotic schemes.

"I don't know," Gabriel replies, looking as though he has no idea why such a thing should matter. "I haven't exactly asked."

"Well now," Sam drawls. "I hate to be a killjoy-"

"Don't see what difference it makes either," Gabriel rolls right over him. "Ever since the first day, Cas has carried a torch for Dean that you can see from Mars. So even if he's not into guys, there is one exception."

"And you can't just… tell them?" Sam asks, a bit desperate. Of course not. That would be no fun.

"I think that if things were going to develop naturally, they'd have been going at it like bunnies for years now," the shorter man says dryly. "Quite possibly from the moment they met. I was there, remember. I could practically hear the blood rushing south." Sam holds up a hand, putting the conversation on hold for a moment while he mentally purges that image.

"And in order to push them together," he says, "you want me to set Cas up with other people?"

"Yes."

Sam considers this for several long minutes. He nods once, after he has turned this gem of a plan over in his mind and studied all the flaws.

"You're an idiot."

"And you're petty and condescending, but I wasn't going to say anything."

Sam would rather swallow his own tongue than admit it, but it is nice to occasionally have an argument with someone who doesn't sound like they're borrowing their riposte from a third grader's repertoire of insults and witticisms.

"So you're trying to make Dean jealous," he says.

"Well, it can't be Cas, it would take months for him to figure it out and years for him to do anything about it. Dean is a little more leap-before-you-look. Also, if I'm completely misreading the situation-" and here he scoffs a little, like such a thing is patently impossible, "-and the whole UST is one-sided, then Cas gets a few dates out of the deal and no harm no foul."

"Did you honestly just say UST?" Sam asks incredulously.

"And it's got to be you because Cas knows better than to go anywhere near anything to do with me. Plus he has this morbid fear of making you cry again, so no matter how crappy the dates are he'll keep at it if you ask him."

The problem with childhood friends, Sam decides, is that they're childhood friends. They've been around a while. They know all the really embarrassing stories. Like the one where, upon their first meeting, thirteen-year-old Cas had managed to make a barely-nine-year-old Sam cry. Sam hasn't managed to live it down, made all the more frustrating by the fact that Cas somehow has.

But that was twenty years ago. Sam has grown up.

"What do I get out of it?"

"Bug the crap out of Dean for however long," Gabriel says instantly, naturally going for that which appeals most to him. "And if all goes well, your brother's sex life will include not having to remember which name to yell out this time. And my brother's sex life will include actual sex."

"If I agree, will you leave?"

"Bearing in mind that wasn't actually an agreement, just an offer of one, yes."

Pain in the ass. "Fine. I agree. Now please," and he gestures towards the door. Gabriel is almost gone, one foot in the hallway, when he pauses and turns back.

"Last thing," he says. "Kinda important. Let Cas be the one to tell Dean you're setting him up with people."

"Gabriel-" Sam begins warningly, but by the time he reaches the third syllable, he's talking to thin air.


The following Friday morning, Dean wakes up half-naked on the couch in Cas' living room. This would be of far greater interest if it weren't for the fact that it has happened every Friday morning for going on three years now.

By this point, Cas has been gone off to work for well over an hour now. Dean had stayed over the previous night, as he has every Thursday night, because he'd drank more beer than Cas was comfortable with and he wouldn't let Dean drive himself home and no way in hell is Dean letting Mr. Totaled Two Cars in Four Years touch his precious Impala. So, as compromise, Dean gets the couch- like there's any competition for it- and Cas tries not to wake him up as he gets ready for work the next morning.

It's harmless and innocent and- to a certain brother- completely frustrating, in the pull-your-hair-out-and-scream sort of way because my God are those idiots blind? What planet do they live on?

The interesting thing is what happened the evening before.


Thursday nights as pizza-and-beer night- minus the beer part, back at the beginning- started way back in tenth grade, when Dean realized that he would need serious help if he wanted to pass his math class. Since it seemed unfair to burden Sam with his woes- which, roughly translated, means Sam had just entered middle school and was appalled at the level of homework they were giving him and wouldn't take the time out of his busy busy schedule to help Dean without a flat nightly rate of twenty bucks- Dean went instead to the other neighborhood brainiac. Cas wasn't necessarily any happier about it than Sam, but by virtue of not being related to Dean, he was considerably politer about it.

And then one night Dean picked up a pizza before coming over, and thus stumbled upon the secret to taming the grumbly snappy beast that is Castiel.

Long gone are the days when Dean needed Cas to help him with his homework. These days, or so Dean tells himself, this is just to make sure Cas has something vaguely resembling a social life, pitiful though it may be. And if it feels like an escape to Dean, a weekly breath of fresh air before diving back beneath the surface, well, that's his problem.

This week is different, though, with Cas feeling a bit off-step all evening, culminating in his frowning intensely at the TV screen as they watch the video of Super Bowl 38 Dean recorded. Dean watches him, a bit worried- hey, he likes football as much as the next guy, but Cas is staring at it as if it contains all the keys to unlocking the secrets of the universe, if he can only discern them from the meaningless background chatter.

"Cas, dude, relax," he says finally, when he's starting to get twitchy himself from Cas' obvious tension. "It's just a football game, all right? There is such a thing as overthinking it."

With an almost audible ripping sound, Cas tears his attention away from the TV and looks over at Dean. Someone may as well have drawn a great big question mark on his forehead, his confusion is that obvious.

"Have you spoken to Sam recently?" he asks plaintively, and Dean suddenly realizes that Cas wasn't watching the game, probably wasn't even seeing anything. Eyes following the lights and movement, like a cat, while lost in his own thoughts.

"Nope. Why?" And Dean takes a sip of beer. In retrospect, he should have known better.

"I think he's trying to set me up on a blind date," Cas says, and Dean inhales beer. The next few minutes are fairly active, what with Cas trying to stop Dean spilling beer everywhere and Dean trying not to die.

Once the excitement has passed, and Dean is breathing again, he asks, "What makes you say that?" Because Cas- and Dean says this with nothing less than the greatest affection- has the social skills of a tree stump. It's easy for him to misread things.

"He told me he was," Cas says, and Dean has to admit, it's kinda hard to misread that. He stares mournfully at the puddle of beer soaking into the carpet and shakes the bottle in his hand. He considers getting another one, then decides it can wait to the end of this conversation. Something tells him the potential spit-takes are still coming.

"Did he say why?" Dean asks next.

"No." And Cas didn't ask, because he isn't hardwired that way.

Dean looks back at the TV. Commercials are running- because what's the point of recording a Super Bowl without them. This is the year, he remembers, of Janet Jackson's legendary 'wardrobe malfunction', and halftime is coming up. He scrambles for the remote and pauses the game. Then he realizes what he just did, implying that this conversation is taking the fore in terms of priorities, when right now he just wants it to go away. He unpauses it, fast-forwards through the commercials and a good three minutes or so of the game before Cas gently takes the remote away and pushes play.

"How long's it been?" Dean asks, as they're skipping through the halftime show, a little bit later. "Since you went out on a real date, I mean."

Cas doesn't immediately answer. His eyes go a bit out of focus, like he's adding up the numbers in his head. Which, really, is an answer in itself. Dean knows better than to comment on it. Having a new date- and he uses the term loosely, most times- every week is about as emotionally healthy, but Cas' approach includes less humiliating doctor's appointments.

"If you, you know, need advice…" he begins, shuffling his feet until he realizes what he's doing and forces himself to stop and pointedly not looking at Cas.

"Ask Sam," Cas finishes grimly, and when Dean starts to protest, he says simply, "Homecoming, senior year."

Dean grins a little at the memories.

"Yeah, all right, I don't really give good advice," he admits.

Cas spends most of the third quarter looking at Dean, long subtle little stares, as if trying to see beneath his skin. It's unnerving, but Dean is used to it, and manages to ignore it while he watches the game and cheers for whichever team he feels like, as if he has any affect whatsoever on the outcome.

Thus was Thursday night.


The following morning, Dean calls in sick- easy enough to do when you're your own boss- and, after a considerable amount of deliberation, heads out to Sam's office. He hears the kid before he sees him, talking to someone around the corner in the hallway just off the elevator. Arguing, really.

"Sam!" he barks, lengthening his stride.

It would occur to someone else, or even Dean at some other time, that there was something somewhat unusual about the scenario he was presented with when he came around the corner. Sam is standing alone, apparently addressing the wall. A door close to the spot Sam had chosen to have his half a conversation is slowly drifting shut. But all Dean can see, locked on as he is like a guided missile, is his brother.

"You know," Sam says conversationally to no one in particular, "when I started working here, they said something about building security, so random people can't just come strolling in."

"Feeling violated, Sam?" the almost-shut door asks softly. Sam glares at it.

"Hey," Dean says as he comes up to his brother, trying to restrain himself. He has nothing to be angry about, he tells himself. Sam is Cas' friend too, even if they were never as close as Cas and Dean, and they're all adults and nobody needs idiot big brother running interference in a situation he doesn't entirely have a handle on.

"Hello, Dean," he says in a false friendly tone. "Did you need something?"

Dean balks for a moment, eying his brother warily. The tone is concerning. Still, this is for Cas, so he pushes ahead.

"Yeah. Cas said something last night, about you setting him up on a blind date?"

"It's just a casual thing," Sam says, shaking his head. "Cas seems a little…"

"What?" Dean says, almost snaps, suddenly defensive. "Cas seems a little what?"

Sam, for his part, is well aware that no one is truly in control of this conversation. He doubts Dean even fully understands why he's here.

"Lonely," he replies flatly. A challenge. "He needs to get out more, make some new friends. Anna is a nice girl-"

"A nice girl? Who are you, her grandmother?" Dean scoffs.

The door snickers. Sam glares again.

"Who are you? Cas' keeper?" he shoots back, refocusing on his brother.

"Look, just-" Dean shakes his head, moves away a bit and paces a step or two. Then he turns back to Sam. "Cas is freaking out about it. You know how he gets, all wide-eyed and crap? He's afraid he's gonna, I don't know, upset her and disappoint you or something."

If anyone says anything about Cas making Sam cry, there will be blood spilled right here and now.

"It'll be fine," Sam assures him. "Just a friendly dinner and- why am I explaining myself to you?"

"Yeah," Dean says, as if any of this has made sense and somehow told him everything he needs to know.

"And now you're leaving," Sam says flatly as Dean turns and heads away.

"Yup. Thanks, Sammy."

"You couldn't have just called? You had to do this in person? Here? Of course you did," he says, muttering the last part to himself, as the elevator dings.

"Oh yeah," the door says. Sam shifts around to face it. He can see, through the crack it has been left open, a sliver of Gabriel's triumphant grin. "He's Mister Cool. Completely unconcerned. Not overreacting at all."

"He's a good friend," Sam says, feeling stupid even as he says it. Gabriel doesn't bother to respond, which is just as well because Sam can hear him smirking.

He's surrounded by crazy people, he thinks in despair, and the crazy is catching.

"Still quitting on me?" Gabriel asks cheerfully after a few moments.

"Fine," he snaps, grabbing the door and swinging it open so he can look the older man properly in the face. "Fine. I will help you with your little scheme, but after that, leave. Me. Alone."

Gabriel only smiles, like he's remembering the punch line to some great grand cosmic joke that everyone who isn't Sam Winchester is in on. It's a very condescending smile.

"Yes sah!" he barks, giving a sharp salute.

Sam slams the door shut in his face.