Dean has been trying to house and feed both him and his younger brother, Sam, since they were kids. It's definitely not easy, especially being a high school dropout with a C-minus average. Taking orders at Mcdonald's doesn't pay well — definitely not enough to feed two teenage boys and add to the younger Winchester's college fund — so Dean has to resort to... less legal methods of earning money.

Dean's an expert at making fake IDs, and he shows it to the bartender with such confidence that she doesn't question his age, instead just sliding over the cheapest drink they have. One may be wondering why a broke teenager is spending his night at a bar buying drinks instead of saving his money for more important things, but he has every intention of leaving with more money than he came in with. The drink is just to make him seem inconspicuous.

Taking a sip of his drink, he looks around subtly for the perfect victim. And... there. He sees her not too far away; a redhead with a pearl necklace and a fancy black shirt, just barely covering the waist of her pants. More importantly than her attire is the wallet sticking out of one of the back pockets. Bingo.

Leaving his drink on the bar, he meanders through the room in a seemingly aimless manner. He "accidentally" bumps into her, muttering an apology as he quickly plucks the wallet from her pants and slipping it into his own pocket. She never even knew what hit her.

He wishes he could go back to the bar he used to go to, back when he could just hustle pool for money, but unfortunately, he got busted for his fake ID. Pickpocketing is all he's got in this pool-less bar. He used to feel guilty about it, but thinking of Sam, curled up in bed at their crappy apartment, is enough to convince him that this is okay. As long as it helps keep Sammy safe, it's worth it.

"Hey," a low, gravelly voice says. Dean looks around to see a man wearing a suit next to him — who wears a suit to a bar? His unnaturally blue eyes sparkle even in the dim lights, catching Dean's eye immediately.

"H — hey?" Dean stutters, then mentally kicks himself for it. He's not sure why he's getting so flustered. He's not here to get laid; he's here on a mission, and that mission doesn't involve seeing this man ever again. Now, where's his wallet...?

The man smiles slightly, and before Dean knows it, that smile is against his lips. Too shocked to move at first, he just stands there, but after a moment, he decides to kiss him back because why the hell not have some fun?

The mysterious man pulls away, a small smirk on his face as he turns and leaves without another word. What the hell was that? He can't complain about a good kiss, but he sure as hell has questions about it.

Dean looks around, searching for another seemingly wealthy person to rob. Unfortunately, the bar seems to be full of drunk hobos with barely a penny to their names. That sounds shockingly like Dean right now, actually, minus the drunk hobo part.

Dean sighs in defeat and reaches for the wallet he stole only a few minutes ago. How much does he have in here? Enough to pay rent tomorrow, at least? The landlord's getting sick of waiting every month. If he's late again, there's a solid chance he and Sam are going to lose their place.

Shit.

His pocket's empty, not a wallet to be found. He literally just took it a minute or two ago. He couldn't have dropped it. Where the hell...?

Oh, that son of a bitch.

That guy he just made out with is over with the redhead, chatting like they don't have a care in the world. Her wallet is back in her waistband, though tucked in a little bit more so it would be more difficult (though far from impossible) for someone to take. It doesn't take a genius to figure out that it was Blue Eyes who stole it from him. It must be nice to be able to steal someone's wallet back instead of just stealing it, but Dean needed it a hell of a lot more than she does.

 As if sensing Dean's gaze on him, he glances over at the boy and winks, a smirk on his face before turning his attention back to the girl. That motherfucker...

So now what? Go try somewhere else? There aren't a lot of other crowded bars nearby, and pickpocketing is harder when the victim is sober and more alert. He'll just have to find another victim here. He just doesn't know how. He needs the money by noon, but with Mr. Superhero here, Dean's afraid he might be leaving here empty-handed.

But whatever. He'll make it work. If he did the math right, he only needs about 60 dollars to make rent. He can make that up in two wallets. Maybe he'll even get a couple extra bucks in the process and he can get Sam a treat tomorrow. 

Dean pushes through the crowd, accidentally bumping into people as he searches their pockets until he finally finds a boy whose wallet sticking out of his pocket. Bingo. People should really stop leaving their wallets out in plain sight -- not that he can complain. He walks by, casually plucking it from his pocket with a quick rustle against him.

He subtly slides the wallet into his own pocket and looks around again. Part of him wants to check how much is in this one, but he doesn't want to draw attention to it. He'll find another person dumb enough to leave their wallet out and swipe that one, then he can get the hell out of dodge and count his profit when he's alone. Two wallets isn't much for him, but maybe he'll come back tomorrow when Blue Eyes won't be around to ruin everything.

Speaking of wallets, there's a girl with one poking out from under her shirt. He pushes through the crowd, not phased by the number of people he bumps into in the process. God knows he's run into a lot of people in his life, so this is nothing new.

He walks past the girl, grabbing her wallet easily and sticking it into his other back pocket as he continues to walk to the exit. It's no less crowded on the way out than it was on his path to the girl, but the fact that he's just moments from making it outside is all the motivation he needs to push through the throng. 

The cold air hits him like a wall. He's always loved the feel of the night air on his skin, but it's always so much more refreshing after spending so long the bar.. It's so hot and stuffy surrounded by all those people. It's almost suffocating, spending so much time in there. It feels so good to leave again.

He leans against the wall outside, his breathing steady but heavier that usual as he allows the fresh air to fill his lungs. He almost wishes he could live outside, but he knows from experience that it's not-so-shockingly less fun when the weather gets bad.

Dean reaches into his pockets to pull out the two wallets and count the money, but there's a slight dilemma. His pockets are empty.

 
"Shit!" he yells, and he doesn't give a flying fuck if anyone hears him. He needed that money tonight. He slides down the wall, burying his head in his hands in defeat.

Now what? Go home and tell Sam to start packing? He's always hated doing that. Just as Sam starts making friends at school, Dean always has to pull him away because they can't afford to stay there. Sam was just telling him about some Gabriel kid not even a week ago. Dean should have known that meant it was almost time to leave. It's like a cruel game fate plays on them, and he hates it.

"You know, if you got a job, you wouldn't have this problem."

Dean doesn't have to look up to know who said that. He may have just met him tonight, but the low voice is unmistakable. It's Blue Eyes from earlier.

"Fuck off," Dean growls.

"I'm just saying, those people have to work for their money. You should, too. Then everyone wins."

"I said fuck off," Dean repeats. He doesn't even have it in him to be mad at the guy. He's just giving up. For today, at least. He has a brother to feed. He can't give up entirely; his brother's future is on the line. 

"I know you did," he replies simply. "And I wouldn't be be talking to you at all, but you stole my sister's wallet."

Dean mentally kicks himself for that. The redhead was his sister? No wonder he stole it back! It explains why the other two wallets disappeared, too: the guy was watching him, keeping an eye out for who else Dean stole from. If he'd just left that first girl alone, he would have more than enough money for rent tomorrow.

"Are you just gonna sit here?" the boy asks. "Cuz if so, I'm just gonna call the police and get them to deal with you."

Dean's head shoots up at that. "No, don't call the police," he pleads. "Please."

The boy scoffs, reaching into his pocket for his cellphone. "You're a thief. Like, an actual thief. I think it's about time someone finally called the cops on you."

"No, please, don't," Dean begs him. "I still have to get my brother food for tomorrow. It's a weekend; he won't get the free lunch at school."

The boy pauses, uncertainty in his eyes as he lowers his phone to his side. "If your brother's getting free lunch, he's gotta be a kid -- and, honestly, I don't know if I even believe that you're 21. Where are your parents in all of this?"

Dean narrows his eyes. "Dead." His voice is cold, and, honestly, it's the reaction the guy deserved. You don't just go around asking people who are obviously struggling about their parents. It should be a safe assumption that the answer's not going to be pleasant.

The boy's curious expression changes to one of sympathy, and Dean has to look away. He hates the sympathetic looks he gets when he says that. He knows it's sad. He doesn't need anyone's reassurance that it does, in fact, suck.

"I'm sorry," Blue Eyes says, like that's going to fix anything.

"Good."

Dean hopes that will be enough to end this conversation. He's not particularly happy with this guy, and really, the only reason Dean hasn't walked away yet is that he doesn't want to go home to see Sam sleeping peacefully in his bed, the last time he'll be able to do so before Dean has to tell him the bad news. Right now, he just wants Blue Eyes to leave him alone so he can sulk in peace.

Unfortunately, Blue Eyes sits down in front of him and it becomes clear that that's not going to happen. 

"How old's your brother?" he asks.

Dean raises his gaze to meet the boy's, ready to make a sarcastic -- and likely borderline-hostile -- remark, but when he sees the look on his face, he cuts himself short. He really does look sympathetic, and it seemed like a genuine question. Maybe he deserves a genuine answer.

"Almost 15," Dean says finally. His birthday is tomorrow, actually, adding yet another layer to the reasons he doesn't want to tell Sam that he couldn't scrape together enough for rent. Still, if he's not paying anything for rent, maybe they can take a few dollars that would have gone towards rent and spend it on a cake instead. 

"Six years younger than you?" the boy asks.

"Four." Dean doesn't even try to lie about it. The guy already called him out for presumably faking his age; this isn't going to come as a shock to him.

"I figured it was more like that," the boy says. He holds out a hand. "My name's Castiel."

Dean doesn't respond. He's not looking for a conversation, and he's sure as hell not looking to make a friend out of the guy that caused all this shit.

"And you are...?" Castiel prompts.

"Leaving." Dean stands up, brushing the dirt from his clothes. 

"Wait." Castiel scrambles to his feet.

Dean sighs and turns around to face him. "You have ninety seconds. Go."

"Why are you in such a rush?" Castiel asks. "'Cause if you're going to steal someone else's wallet --"

"I'm not," Dean snaps. "I have to go home and start packing."

"Where are you going?" Castiel asks. 

"Why are you asking so many questions?" Dean counters. 

"Because I'm curious," Castiel replies simply. "Why are you avoiding my question?"

"Because it's none of your business where I'm going." He turns around to leave, but Castiel grabs his wrist and stops him. "God, what do you want?"

"My ninety seconds aren't up," Castiel replies. "Where are you going?"

Dean pulls his hand loose with a sigh. "I don't know, okay? There aren't a whole lot of cheap places around here, so probably my car until the school year's over." The least he can do is give Sam the option of finishing the last month and a half here before they move on. It will give him time to collect some money, too, so they can have a little bit saved up for their next shitty apartment. 

Castiel tilts his head in confusion, squinting his eyes slightly. "Where are you staying now? Your car?"

"No, I can't get evicted 'til two weeks after I get the notice that I already know I'm going to get tomorrow," Dean says. "I still got 15 days."

"You're getting evicted?" Castiel repeats. 

"Well, someone took my rent money, so yeah, I am," Dean says. "Thanks for that."

"Well, to be fair, it was my sister's money," Castiel reminds him. "It's not like I stole your money -- and, for the record, I do think rent is supposed to come out of your own money, not random strangers'."

"Well, I don't get paid for another week and I'll still be a few bucks short," Dean says, "so spending your sister's money was my next best idea."

"Ah, so the friendly neighborhood pickpocket does have a job," Castiel remarks.

"No, I make all my money hustling pool and stealing people's wallets," Dean says sarcastically. "Of course I have a job."

"Where?" Castiel asks, then adds a quick, "if you don't mind me asking."

"I do mind you asking, actually," Dean says. It's not that he's embarrassed to admit that he barely makes minimum wage fixing up cars at the garage; he just doesn't want to give this guy the satisfaction of getting an answer out of him. He walks away, hoping Castiel will take the hint. He probably does take the hint, honestly. He just chooses to ignore it.

Castiel walks beside him, his hands in his pockets. "Where are you off to now?"

"Does it matter?" Dean asks, exasperated. "What, are you just going to try and stop me again?"

"Are you going somewhere that I should stop you?" Castiel asks.

"I'm just going to the grocery store," Dean says. "I don't think a billion-dollar corporation is going to care if they notice a box of cake mix disappeared." He'll head back tomorrow after work to lift a container of frosting, and that should be all they need for a cake. It might not be a very good cake, but a shitty cake is better than none, right?

"You're going to the grocery store," Castiel repeats skeptically. "Which is why you're heading away from the parking lot. Uh-huh."

"Dude, have you seen gas prices lately?" Dean scoffs. "I was not going to drive here when it was only a 45-minute walk." And the grocery store is on the way home, so that won't add too long to his trip.

Castiel cocks an eyebrow. "You walked 45 minutes here just to steal some wallets?"

"Yeah, fat lot of good that did me," Dean deadpans.

Castiel frowns. "You know, this isn't a very good area, especially at night. I can drive you to the grocery store."

Dean rolls his eyes. "I can handle myself. I'm broke, not weak."

"I know," Castiel says quickly. "I know, I just..."

"You just what?" Dean snaps. "You wanna bother the poor guy? Well, get in line."

"No, actually, kind of the opposite," Castiel says. "I feel bad. I didn't realize..."

"I don't give a rat's ass how you feel," Dean says. "Now, if you'll excuse me, I gotta get to the grocery store before they close so I can bake a cake before work tomorrow."

"You're never gonna make it on time if you walk," Castiel tells him. "Come on, let me drive you."

Dean stops walking and crosses his arms. It takes Castiel a moment to notice, and he backtracks, standing in front of him with his head cocked to the side. 

"Why?" Dean asks.

"Why what?"

"Why are you so dead-set on 'helping me'?" Dean asks. "You've already fucked up my plan. You can't fix that by offering me a ride."

"I know," Castiel says. "And I'm sorry about that. I mean, I definitely don't condone stealing from people, but I can see your side of it and I feel bad. I figure the least I can do is go buy you your cake mix."

Dean raises an eyebrow. "So now not only are you trying to drive me to the store, but you want to buy my food for me, too? And you're doing it all out of the goodness of your heart?"

Castiel shrugs. "I guess so."

"Bullshit," Dean says. "No one just does that just because they can. What game are you playing?"

"I'm not playing any game," Castiel says. "I don't know how much clearer I can make it. I want to help you because I feel bad. It sounds like you're dealing with enough shit as it is. And you're cute. But if you really want to run all the way to the grocery store just for a chance at making it before they close, I'll back off."

Dean rolls his eyes. "Well, thanks, but I'm not interested -- in you or the ride."

"Not for nothing," Castiel remarks, "but you seemed pretty interested in me when you kissed me."

Dean doesn't bother pointing out that technically, Castiel kissed him. Instead, he says, "You just wanted your sister's wallet back. That's all it was."

"You didn't know that," Castiel reminds him. "Now, I'm not going to test this theory because I do value consent, regardless of what that spectacle back at the bar may have implied, but I have a feeling if I kissed you right now you might just change your mind."

Dean purses his lips. If he didn't have other places to be, he might have taken Castiel up on that. He hasn't gotten laid in way too long thanks to his shitty work hours and even shittier (and rarely empty) apartment. Still, he has to admit, he did really enjoy the feel of Castiel's lips on his, and he'd be lying if he said he wasn't getting a little desperate for any type of non-familial affection.

"But, again, it's up to you," Castiel says. "If you really are going to walk, though, you should probably get started now. You're really cutting it close."

Dean hesitates. He knows he shouldn't get in a car with someone he doesn't know, and he definitely shouldn't get in a car with someone that he would lowkey fuck if he got the chance, but still, Sam's birthday cake is on the line, and it really is a nice offer. And if they just happen to get physical in some way... well, what happens happens, right?

"You know," Dean says finally, "I probably could use a ride."

Castiel smirks. "Interesting time to change your mind."

"Well," Dean says, "you did make some compelling points."

"At the risk of ruining whatever it is going on here," Castiel says, "I happen to have cake mix at my place if you want to bake your cake there. I'm sure we could find something to do while we wait for it to come out of the oven, if you catch my drift."

Dean shakes his head, a small smile on his lips. "I can't tell if I like you or if you just annoy the shit out of me, but I definitely feel some way right now."

Castiel chuckles. "I wouldn't blame you either way."

"And, to answer your question," Dean adds, "I would love to make a cake at your place."