Author's Note: I got this as a prompt on tumblr and I couldn't resist. This is AU by the way, Sam is an aspiring lawyer and Dean is a mechanic. Imagine they're all somewhere in their twenties and you should be good. This is also a work in progress, there will be plenty of chapters.

"Well that's our show. Three guys, three pranks, three million people laughing back at home. I'm the Trickster, and let's hope you're not the next poor sap who gets onto this show. Until next time, stay classy."

Just as Dean reached for the remote to turn off the tv, Sam stalked in the front door. It's not as if he didn't expect his brother to be all grumbly when he walked in, no he's always like this. He was just sick and tired of it- he's the one who chose to go to law school for eight fricken' years. Dean just didn't understand it, why would you go to school when you had the option to not go to school. He has a steady job at Uncle Bobby's garage, so he doesn't see the need to do any more work.

"Heya, Sammy. Why dontcha come sit down, drink a beer? Justice is on next again. New episode, I heard they're planning on shaving some guys head this week." The thought alone had him grinning at the memory of their prank wars when they were younger- Dean had played a particularly brilliant prank where he replaced Sam's shampoo with Nair and made him bald for months.

Unfortunately it had the opposite effect on Sam and he just scowled at his brother before walking into the bedroom, clutching his briefcase, mumbling something about "work" and "no time" and "killjoy." Okay, so maybe he hadn't said the last one, but he was definitely acting like one.

Halfway through the night's second episode of Justice, Dean had an idea. The show was for up-tight sons of bitches who need to be taught to relax, right? Well that description fit Sammy to a T. So why not get him on the show? Maybe he'll finally learn how to have fun for once. He called the number that flashed on screen at the end of the show and gave the people on the line a description of his brother. After only a few minutes, his call was redirected and he was put on the line with none other than the Trickster himself.

"So I hear you got an innocent tight-ass waiting to be loosened up?"

Dean smirked and told him all about Sammy, how he never goes out, how he never drinks or parties, how he hasn't even had a girlfriend in over five years. Hell, he hasn't even been laid yet! Dean had that covered in the seventh grade. The kid had a hell of a lot of learning to do, and lucky for him, the Trickster was all too willing to help.

Gabriel, or the Trickster rather, lived for these moments- the moments in which he met with the people he'd be pranking a few days afterwards, not expecting a thing until the moment they've been tricked. He'd talked to a very nice man the day before, about a guy who could definitely use a prank or two, and was slipped a hint, that the man made a visit to the same coffee shop, at the same time every day, getting the same thing, even sitting at the same table. So here he was, in that very same coffee shop, looking for the man he was to be dishing out justice to.

The description he had been given was "tall, shaggy haired, and lanky." He couldn't really tell height too well, given that all of the customers were sitting down; but if the long, dangly legs cramped underneath the table were anything to go by, he'd assume that the man surrounded by papers spread all over his table was his guy. The first thing Gabriel noticed was how attractive the man was. He wasn't afraid to admit it. Okay, he may be a little bit gay, but come on, who isn't? And this man here? He could make even a straight man whip his head around for a second look. He smirked to himself; oh this is going to be fun.

Lucky for him it seemed like this café was extremely popular, and very busy, seeing as every single table was full. Even better, it made his job a hell of a lot easier. He went up to the counter and ordered a coffee with extra cream and sugar. He impatiently tapped his foot and whistled a low tune, earning himself a glare from the cashier. He just shrugged off the look and handed over the money for his coffee- which was more like dessert than a drink.

"Hiya, kiddo. You mind if I sit here? All the other tables are full." He gestured to the crowded room for full effect. The man simply blinked up at him for a few seconds before seemingly coming to his senses and looking down, cheeks tinted. Gabriel bit back a smirk.

"Sure, just let me move my things." He started to gather all his papers as Gabriel plopped down into the booth opposite him, knees almost touching. He held out his hand.

"I'm Gabriel. You are?" The man looked at his hand for a moment before reaching his out to shake. Gabriel couldn't help but notice how small his own hand seemed in comparison.

"I'm Sam. Winchester." Sam. Gabriel turned the name over in his head a few times, trying to tell his brain to remember this one.

Gabriel hadn't realized he'd been staring until Sam raised an eyebrow. He returned the gesture by arching his eyebrow up even higher. They had an intense staring contest for a few moments before Sam flushed slightly, looking down again. He seemed to do that a lot. Gabriel smirked in victory and plowed on.

"So what do you do for a living, Sammy boy?"

"Well, I'm in school to be a lawyer. I'm only in my fifth year, so I got three more years to go, but it's hell man. I don't know why I ever chose this." Sam ran a distracted hand through his hair, trying to tame it, but it ended up only making it messier. For a moment, Gabriel almost felt bad for the man, until he realized that in two days time he'd be pranking this guy, making his life even more of a living hell. Then he'd really feel bad for the poor kid. Usually, he was only pranking stuck-up kids who think they're too good for everyone, unlike Sam.

But he managed to push that unpleasant thought back, and was already thinking of methods, locations, and supplies needed to pull the perfect prank on Sam.

"Ouch, sorry about that. I never went to college, so I have no idea how you feel. But I haven't been to school in over seven years, and if what you're feeling now is anything like how I'd feel if I suddenly had to go to school, you may as well off yourself now." He placed one hand behind his head and leaned back, sipping his drink. To his surprise, Sam cracked an adorable smile. Gabriel noticed he had dimples; he liked dimples. He liked them very much.

"Yeah, thanks. Real encouraging to hear. Thanks a lot… Gabriel, was it?"

"Yup. And no problem, I'll be here all week if you want any more positive encouragement." He smirked, briefly flicking up his eyebrows, just before taking another sip of his coffee-turned-sundae. Sam looked up and promptly snorted in a way that absolutely should not have been cute. Gabriel just stared at him, face probably showing his confusion, until Sam had stopped snickering long enough to answer his questioning look.

"Your… your lip." He eventually managed to gasp out, pointing at his upper lip. Frowning, Gabriel reached to wipe the back of his hand across his lip, touching something wet and foamy as he did. When he pulled his hand back he noticed that some of the whipped cream from his coffee came back with it. He'd given himself a whipped cream mustache.

He couldn't help it; he laughed too. The kid's laugh was infectious. It wasn't really that funny, but Sam looked like he needed a laugh, so he let him. He didn't seem too much like the man that had been described to him over the phone, however. He was told he hadn't laughed, hadn't even cracked a smile in days. Yet here Gabriel was, making him smile, easy as pie.

Well, until he left. As Gabriel started to get up, thanking Sam for the company, he saw his eyes get duller. All laughter left him as he hesitantly waved and said goodbye. Looking over his shoulder on his way out the door, he saw Sam sigh and type lethargically on his keyboard, rearranging the papers back over the table. His back was hunched and his shoulders slouched. This kid needed to loosen up, bad, and Gabriel was going to make sure of it.

Sam was still scowling at his laptop; in fact, he'd been doing so for the past ten minutes. He was completely at a loss with his paper. For the millionth time, he wondered why the hell he'd decided to try and become a lawyer in the first place. Even on a good day, he barely was able to get a moments rest.

Closing his eyes, Sam rolled his shoulders and allowed himself to relax for a moment. He thought back to the adjective morning at the coffee house a few days ago, where he had met Gabriel. He didn't know what it was about the man, but he made the air around Sam feel lighter. He had just started to get lost in thoughts of gold eyes when-

"Funny seeing you here again." An amused voice broke through his reverie.

Sam immediately straightened and turned to face the intruder, going slightly pink around the ears when he saw the same gold eyes he had just been dreaming of. He really needed to stop blushing around this guy.

"Yeah, I come here every day. Helps me think." He fought to keep his voice calm as Gabriel plopped into the seat across from him, as if this was something that happened every day.

"Think about what, Sammy?" Gabriel replied easily. Sam was surprised, and secretly pleased that Gabriel remembered his name, so much so, that he didn't even notice the use of the nickname.

"You know, just... things." Sam went pink again, when he remembered exactly what he had been thinking of this morning.

Gabriel gave a smirk at that, but didn't question further. Sam took this as an opportunity to question Gabriel in turn.

"So, why are you here? I hadn't seen you here before the other day."

"Good coffee, nice area, cute patrons. What's not to like?" Damn it, there he goes again, blushing like a teenage girl. He really had to stop that.

"But really kiddo, I only stopped by hoping to find you. You forgot something the other day." Gabriel just looked at him with a glint in his eye. Sam could have sworn he left after Gabriel did, so how could he have left something? He raised his eyebrow, but got no response other than a smug smile.

"Alright, I'll bite. What did I leave?"

"This." He pulled out a piece of paper and laid it on the table in front of Sam with a wink. "See ya' later Sammy." He gave one final smirk before getting up and quickly leaving the coffee shop. Sam was so busy staring after Gabriel, he almost forgot about the paper. He grabbed it and slowly unfolded it, not believing what he saw inside.

It was a phone number.

Sure, Sam had been given phone numbers before. But he'd never gotten one from anyone as interesting as Gabriel before. He'd usually gotten them from slutty women at bars, which brought up two problems. One, he wasn't really all that interested in women in the first place. Two, they were all the same- hit it and quit it, give you their number and if you call, great, if not, your loss. Now that he thought about it, Gabriel seemed sort of that type too. He didn't know if that was a good or a bad thing, but he was pretty sure he wanted to find out more about the guy.

Well, at least he knew he wasn't getting any more work done right now. With a small smile, he packed up his things and headed for the door, thoughts of golden eyes filling his head all through the day.

When Sam stepped inside the house, Dean hurriedly bid someone on the phone goodbye and threw the phone on the seat next to him on the couch. He was never one for subtlety. He threw Sam a quick glance before turning back to the TV as if nothing happened.

"Hey, Sammy. How was school?" Sam merely shrugged, and plopped down on the couch next to him.

"Fine, I guess. Normal." Dean stared at him for a moment while Sam raised a questioning eyebrow.

"Normal. Sam, normal for you is grumbling and slamming the door to your room. This, nu-uh. This is not normal." Sam shrugged again.

"I dunno what to tell you, Dean. Hey, who was on the phone?" Dean's eyes widened a bit as he stumbled for an answer.

"Uh… no one. No one important. Don't worry about it." But when he put it like that, how could Sam not worry about it?

"Come on, Dean. Who was it? Was it someone special? Girl or boy? What's their name? Come on, spill."

"No, Sam. It wasn't anyone special just… my friend asked me to go to the bar with him tonight. He said to invite you, too, said his cousin was in your Sociology class. Cas-something, some weird-ass name." Sam only had to think for a moment.

"Castiel? Oh yeah, I know him. He's pretty cool. Sure, I'll go. What time?" Sam looked at his brother to find him, once again, gaping like a fish. "Oh come on Dean, close your mouth. It's not attractive."

Dean snorted and threw a pillow at him, which Sam easily dodged.

"Bitch."

"Jerk." Sam smiled at the usual banter.

"Anyway, they said to meet them at nine. Unless, of course, you need your beauty sleep. I know how much you hate going to bed after 8." Sam retaliated with a flick to the ear.

"Ha ha, very funny. I'm gonna go get some work done in the mean time." As Sam walked to his room, he could've sworn he saw Dean pump the air with his fist out of the corner of his eye. He decided to ignore it for now.

When he sat down on his bed, he immediately went for the slip of paper in his pocket. Was it too early to call him? How about a text? Sam hadn't actually had a date in years, so he wasn't quite up to speed with the etiquette involved. And he sure as hell wasn't asking Dean for dating advice.

With a sigh, he decided to leave the call for later and try to actually work on his paper. That plan was quickly dashed as he fell asleep shortly after laying down with his laptop. He awoke with a start to Dean banging on the door.

"Wake up, Sleeping Beauty. I'm leaving in five minutes with or without you." Sam groaned and blinked away the sleep as he swung his legs over the side of the bed. He padded over to his closet, thanking the gods he wasn't like Dean, who took twenty minutes just to decide on a shirt to wear. He quickly got dressed and grabbed his phone before running out to the living room.

"Finally. Jesus Christ, I swear you could sleep through an atomic bomb." Dean continued mumbling all the way down to the car.

The car ride down to the bar was relatively uneventful, but full of Sam's questions about Dean's not-date. Sam was sure it really was a date, whatever Dean called it, he's just always had problems with relationships.

When they walked into the bar, Sam wasn't sure what he was expecting, but it sure wasn't Gabriel, sitting with Cas in a booth nearby. He just stared at him for a minute before Dean kindly reminded him to "Fucking move, damn it."

When they approached the booth Gabriel and Castiel were sitting in, Gabriel jumped up with a wide smile.

"Heeeeey, Sammy! And Dean-o! Come on, take a seat!"

Gabriel stepped aside to allow them to enter the booth- Dean slid in next to Castiel, leaving Sam to take the empty side. As soon as he sat down, Gabriel slid up next to him, closer than strictly necessary, and called over the waitress. And if their legs were maybe touching under the table, Sam sure wasn't gonna make Gabriel move.