Chapter Text
Dean and Sam lived in the octagon house on Spruce Street. Surprisingly enough, that was a pretty successful pick-up line that they were both slightly ashamed to say they’d used repeatedly. Apparently, after midnight, certain drunk girls were intrigued when they found out a hot guy’s bedroom may have more than four walls. Other girls knew it was a notorious party spot. To them, saying you lived in the octagon house was essentially touting your good reputation for offering up a safe one night stand with absolutely no chance at ever getting called back for a second romp. It was the phrase of doom for any girl who had monogamous designs on Sam, who had been known to get all squishy and dateable a time or two, but never with his walk-of-shame victims.
For Dean, it was freedom. Freedom to finally stop performing and get down to business. He didn’t know how girls did it, day in and day out with their clothes and their makeup and their bubbly personalities. He had enough trouble smiling and grimacing on cue during a 15 minute open mic. By the time he'd sat through Sam and whoever else was on the hook that night, he was thoroughly fatigued from whispering his criticisms of the crowd and the performer alike, to no one in particular. He was then expected to bullshit his way into bed with the cutest girl who casually complimented his set? Fuck that noise. "Did you know I live in the octagon house?" was about all he could muster at that point. It hadn’t failed him yet, (but who are we kidding, his perfect fucking face helped his game about three times as much as it hurt his act).
Comedy. It's what Winchesters did. Winchesters, and about a million other dumb fucks with an iPhone and 140 character witticisms about their first world problems. It was not supposed to bug Dean when no-talent "wordsmiths" got highlighted in a bit on Ellen or Bob and Tom. But it did.
His dad John, well he was great at it. It was dark comedy. It came from a dark place; the loss of a wife and the life of a morally bankrupt single dad, almost innocent in how thoroughly unprepared he was for fatherhood. Substance abuse in itself provided jokes for days. The material actually outlasted his dear old dad. This surprised no one. What was surprising was Sam's decision to ditch college and do his own act, despite his lingering bitterness.
At first, Dean was sure that that was all he was gonna hear in Sam's jokes - slams against his dad and his childhood and how ruined Sam was for "normal" relationships thanks to all the bullshit. The best comedy was supposed to come out of the worst experiences. But just because Sam quit school didn't mean he'd forgotten how to be a genius. John Winchester was a jerk, but he was a full fledged performer. An entertainer. An artist. And Sam was his son, apparently also not content to let the coddled one-liner tweeters of the upcoming generation completely obliterate the art of stand-up comedy. Sam knew intrinsically what mechanisms were at work in a good routine, and Dean never felt more proud of his little brother than he did when he watched his first open mic.
"First off, I need to apologize." Sam started, with a mischievous sad puppy face. "I'm incredibly tall." The kinder, looser audience members giggled. "I had no idea, until someone told me earlier, backstage.” He gave them a look of sheer naivety, then let it crack into a knowing smirk. “I love being told that. It saves me from giving two shits about how I look. Who cares, right? I’m a walking Rorschach inkblot that provokes ‘tall’ in 90% of the population." He shrugged. "I can handle that." He fiddled with the mic stand in an expert way that might have been embedded in his genetic code. "Because I know there is going to come a time when people will meet me and NOT tell me I'm tall, and that will mean that I have a new defining trait. Something that you are not allowed to just blurt out at people, like 'In an earthquake, I would be afraid your forehead might topple over and crush me!'" He put on a funny, high pitched voice for his quoted bits. "I could always just assume that people's first thought is 'wow, he's so handsome!' Because, unfortunately that's just not something we, as men, feel comfortable telling each other- which is just too bad." Sam smiled his most winning smile.
"You're hot!" A drunk girl hollered from her seat at the bar. The audience tittered.
“You see? Thank you.” Sam gestured towards the voice. “Your voice is very feminine.”
Dean wondered if Sam would lose his footing after bantering with the hecklers- if the whole set was just a randomized list of pleasant observations. He didn’t wonder long, as Sam began to quickly weave an engaging story of puns and quips with only occasional pauses to allow the callbacks to his previous lines to pierce through the drunkenness and hit home. Of course. Only Sam would start off a 10 minute slot at an open mic as if he were carefully easing himself into an hour long HBO special. Dean was clapping the loudest, with a tear in his eye when Sam finally waved and said, “well, that’s my time,” hopping off the 8” stage, and still towering over the audience, perched at their high tables.
“How was it?” He asked Dean, slicking his hair back with two hands for no reason other than nervous movement and the dispersion of sweat.
“It was awesome. Seriously. You got the gentle giant thing going, then you hit ‘em with the sarcastic stuff later. It was great.” Dean patted his brother on the shoulder. “You wanna get out of here?”
“Nah, let’s stick around. I wanna drink. I’m jittery.” Sam was off to the bar with a nod.
The first night Dean saw Sam perform was also the first night Dean saw Castiel perform. He was the next guy called up to the stage by the wild and zany open mic host. Sam had brought Dean a beer and Dean was content to have zoned out for a minute, until a very serious, and gravely voice came through the PA.
"Thank you for that colorful introduction, Gabriel. Hello. I am Castiel. But first, let’s hear it for Sam. He was ...handsome." The crowd whooped for Sam, and appreciated Castiel’s callback.
Dean smirked, and took a moment to stare down this Castiel. He was tall, with dark hair and a five o’clock shadow that highlighted his angular jaw. He was dressed in a white shirt and black slacks that could have been purchased at Wal-Mart, all partly obscured by a tan trench coat that might have cost a lot when it was new, twenty years ago.
“You will have to excuse me if my people skills seem a little rusty.” Castiel continued, examining each member of the front row with unbridled intensity. “I was adopted by very strict religious parents, and home-schooled all my life so that I could become a valiant soldier in the Lord’s army.” People literally groaned out loud. “There were 12 of us. My mother originally only wanted three children, but someone was kind enough to tip her off to the desertion statistics for this particular war with the devil. ”
“In addition to beating us with a belt when we misbehaved, and forcing us to memorize long passages of scripture, my mother could also be cruel." Dean didn't know if uncomfortable laughter was desirable, but it was becoming bountiful.
"She was strongly against vanity, but she discovered the intrinsic value of orthodontry as a form of punishment." He licked his perfect teeth, seemingly lost in thought. “She nearly rejoiced herself off the porch and into the rose bushes when she heard my eye teeth were impacted.”
Dean cringed. Everyone probably cringed. Teeth are a sensitive subject, and the thought of a parent (albeit adoptive) delighting in the pain they cause was rather grotesque. Castiel did manage to lighten it up a little, with anecdotes about the absurdity of the concept of heaven. Dean was smiling, not exactly laughing out loud, but appreciating.
“If you are looking to turn a child off to an entire religion in one fell swoop, I would suggest informing them that the family dog does not have a soul, and will therefore not be admitted into heaven. I have it on good authority that that child will never again worry about gaining admittance into heaven.” Castiel nodded and stared, as if he were relaying the text of the US census.
"I may return to religion in fifty years or so. From what I have read, by that time science will be advanced enough that we can collect a few weeks of communion bread and wine and engineer a new Christ. Do not get too excited." He gave a particularly tall girl in the middle if the audience a stern glare. "It might be awkward during the beginning phases when they haven't quite worked the kinks out. They may have Christs that only last hours, or maybe days at a time. There might be a Dolly the Christ. I suppose they could try to grow his organs in a genetically modified pig. I'm sure the Jews would find that offensive, but what better way to exercise man's dominion over the animals?"
The audience all suddenly became perplexed. Dean could feel their brains at war with their smiles, holding back confused laughter for fear it wasn't entirely correct to find his bizarre statements funny. Castiel smiled for the first time as he also observed their confusion. His eyes crinkled around the edges and his teeth were perfectly white.
"Ah. I have never been able to figure out an acceptable end for that joke. If anyone can, please let me know after the show. Go out with a crash, right? Isn’t that what they say? That is my time. Thank you. "
A smattering of applause, and a few good-hearted cheers followed Castiel off the stage. He weaved around the crowd to the bar, then turned and approached the little hallway to the bathrooms where Dean happened to be leaning, his arms crossed over his chest.
“It’s ‘with a bang’.” Dean half-shouted at Castiel as he breezed by, trench coat billowing behind him, as yet undecided about appearing heroic, or possibly like a crazed gunman. Castiel stopped abruptly and turned to face Dean.
“Excuse me?”
“You’re supposed to ‘go out with a bang’.” Dean’s voice rose at the end of the statement, suddenly unsure as to whether Castiel had purposely butchered the saying.
“Oh. Alright. Do you know what bang it is referring to?” Cas furrowed his brow. Dean scratched his chin, absently.
“Uh. I’m not sure. It’s just how the saying goes.” He squared his shoulders. “I have an end for your Christ-in-a-lab joke too.”
Castiel tilted his head forward, turning his face away so that his ear could be closer to Dean’s mouth. Dean took it as a sign to continue.
“Well I haven’t gotten your cadence down, but you could do a play on those accident signs in factories-” Cas’s eyes squinted at nothing as he still gazed at the bar. “- you know, something like ‘this lab has gone 25 days without killing the savior of mankind’.” Castiel straightened up and peered at Dean with clear, blue eyes.
“What do the signs usually say?”
“Uh, they usually say ‘this factory has gone blank days without an accident’.”
“And then a foreperson fills in the correct number?”
“Well yeah.”
Castiel glanced at the floor for a moment as he scratched the back of his neck. Dean just stared, because he was knee-deep in one of the most awkward conversations of his lifetime, so he figured he might as well make the most of it.
“Where do you live?” Cas asked, finally.
“The octagon house.”
Cas’s face brightened, and he began to look mischievous.
“Now that I have heard of. You’re Dean Winchester.” He grinned as if he thought he were incredibly lucky.
“That’s me.”
“Is there any chance you’re looking for a roommate?” The curiosity burning in Cas’s eyes could only mean that he was very interested in living in the octagon house. Or with Dean. Or with Dean and Sam. Well that was strange.
If Dean had simply taken Castiel’s phone number and let his conscious mind be in charge of his decision making process then Castiel never would have received a callback from the famed Dean Winchester. But as it happened, Dean and Sam had a full one and a half empty bedrooms (there was heated debate still raging about whether the ½ bedroom was really a very large, triangular closet). They were making ends meet with the bits of this and that, plus their comedy, but winter was on its way and winter was never kind when you lived in a house that was more than 75 years old.
“I’d be willing to pay my share of the rent, as well as the full cost of heating. I’m fiscally well-established, but I’m looking to make connections in the business of comedy.”
Alright, he just read my mind. Dean thought, as he stood there gaping. That’s not creepy, right? If anything, it’s useful.
“Forgive me if this is forward, but it seems that you and your brother could be very useful to know.”
Fortunately, Sam saved Dean from visibly short-circuiting right there in the Laugh Shack hallway.
“Hey, Dean, you’ve met Castiel! Hello, Castiel. That was a good set!” Sam smiled, and the hallway to the bathrooms looked a little less dank.
“Thank you, Sam. I enjoyed yours as well. Your brother was just helping me with the end of mine. He is very astute.”
“Really?” Sam made a show of looking impressed. “Dean never helps anyone. He must have really liked your stuff.” Sam gave Castiel a good-natured clap on the shoulder, and Castiel grinned in response. Dean felt that he now needed to squint in the sunshiny light of the hallway.
“That’s so far from the truth, it’s not even funny. I help everyone. If half the people I gave advice to bothered to take it, they wouldn’t still be hosting open-mics in Kansas.”
Dean raised his voice as the evening’s host came flitting by. The man was older than Dean by at least ten years. He was in a purple crushed-velvet blazer and black slacks that had their own sparkly sheen, and for some reason he was wearing a very undersized top hat perched askew on the front of his head, attached with a chinstrap.
“Sucking less cock and writing more jokes is advice my mother could have given me, Dean-o! Now I just plug my ears and go ‘la la la la la are you famous yet? Call me when you’re famous’.”
Dean just shook his head, with Sam mirroring the motion. Gabriel spun away to harass a cocktail waitress while Castiel’s expression became pensive.
“I have been known to sleep with both genders, rather indiscriminately. Would that be a problem?”
Sam’s eyebrows jumped to his hairline for a moment, before he had a mental ‘aha’ moment and collected himself.
“So you asked Dean about renting a room?”
Castiel nodded.
Dean spent a fraction of a second being irrationally angry that Castiel did not simply decide after a 20 word conversation with Dean that he absolutely needed to live with Dean. Instead, Castiel had established some kind of previous rapport with Sam, and they had presumably discussed the pros and cons of the idea, before even considering bringing the matter to Dean. But because these thoughts occurred in only a fraction of a second, they were nearly subconscious, and Dean was simply left with the feeling one gets when one discovers an attractive individual was NOT just winking at them.
“Well look, Cas. I’m not sure if we’re looking for a roommate, but I can speak for my brother when it comes to your sexual proclivities, and any orientation is totally fine.” Sam patted Castiel on the shoulder again, more gently this time. Dean returned from his trip to boohoo-ville, and decided that Sam needed to be put back in his place, after running around offering up rooms in their house without consulting him. Two could play at this game.
“Yeah that’s not a problem. We are definitely looking for a roommate, and as far as I’m concerned, you can move in any time. What is today? The 20th?” He pointed at Sam and raised his eyebrows. Sam nodded slowly. “Great. Yeah you can be in by next month if that works for you.”
“This is excellent news.” Castiel smiled gratefully, and Dean’s heart melted a little, as if he didn’t just welcome a rich stranger into his home so that he’d have an excuse to keep the house at 70 degrees fahrenheit all winter long.
“Wow. That’s awesome.” Dean strained his ears in an effort to figure out if Sam was being entirely genuine. “Welcome to the octagon house, man.” Castiel beamed, and ducked his head.
“I’ll get us a round to celebrate. But first, I’m going to use the little boys room, as I originally intended.”
Castiel breezed away towards the smellier end of the hall, and Sam cocked his head at Dean.
“You’re okay with him moving in with us, just like that?”
“Why not? I assume you vetted him before telling him to ask me about the empty rooms in our home.” Dean glared.
“He seems cool. I mean I didn’t get references, but I told him you’d have to think about it. You didn’t have to give him an answer right then.”
Dean dug a piece of pretzel out of top molar, with his tongue, and scowled a little, turning away from Sam and pushing on his rolled-up sleeves.
“Yeah, well. What’s done is done. If he sucks, the chances are he’ll get sick of us before we get sick of him.”
“Yeah. And if it doesn’t look like he wants to leave, we can let Garth take the other bedroom.” Sam stared at the stage as he said this, where a very tall but gangly man-boy was pulling a sock puppet onto his hand the way a doctor slides into a rubber glove.
“Who wants to hear Mr. Fizzles tell some dirty jokes?” Garth asked with an infectious grin.
“You mean the three walled closet that you have to go through the third bedroom to walk into?” Dean smirked as he watched Garth suffer through the world's cheapest ventriloquist act.
“It also has a door leading to the bathroom!” Sam insisted.
“Sammy. Seriously. No one wants to access their bedroom through a communal bathroom!”
“And no one puts a door to the bathroom in the back of a closet!” Sam punctuated his point with a flap of his hand.
“There’s only one wall that you could even attempt put a bed against, and either way it’s going to block a door. Forget a dresser."
“There’s a window! What closet has a window?”
“It’s stained fucking glass!”
They quickly decelerated after reaching their usual stalemate, just as two cold beers were pressed into their hands, and they noticed Castiel standing in front of them with his own brew. He was glancing back and forth between them with a curious grin. Dean sighed, shook his head, then toasted in gesture only. Sam and Castiel followed suit, and they all three drank quietly, contemplating what exactly had happened, and how it was going to change their lives forever.