At some point, Dean teaches Cas how to play pool. He doesn't mean to teach Cas how to pool hustle as well, not after what happened with poker, but somehow it just happens. They're in the back of the local watering hole and Dean has just finished showing Cas how to hold the cue when a couple of locals walk in, looking very annoyed at the sight of the occupied pool table.
Tonight must be Dean's lucky night, because they've been running out of cash and those two guys look like they're about to make a willing donation to the cause of poor needy hunters, especially the frowny one with designer clothes and tasteless ring. Dean tries not to grin too widely when he suggests that the four of them play a game. He figures it doesn't matter if Cas plays badly, the two strangers will only be goaded into betting more and then losing it all in the second or third game when Dean stops feigning incompetence and uses all of his skill.
The plan spectacularly fails to go as predicted when Cas starts pocketing one shot after the other. The two stooges are actually good at pool, Dean is a bit better, but Cas could best them all with one hand tied behind his back. It ends with the three of them standing to one side while Cas does trick shots, and Dean's mouth is too busy hanging open that he doesn't even think about goading the guys into betting more, though tall dark and loaded is more than happy to supply, going as far as betting five hudred dollars on a shot that Dean's fairly certain no man could pull off.
It's probably a good thing that Cas wasn't human to start with, then. He pulls it off. "Never seen anyone play so well in all of my life," the stranger says, handing over his money to Cas. When he and his friend leave the bar, Dean feels a bit like he's the one being hustled because he's not sure of what just happened.
Cas looks puzzled as well. "Is it all right for them to give me all this money?" he asks.
For once, Dean doesn't need to lie. "You won it fair and square," he says, patting Cas on the back. And good thing that Cas did, too, because Dean was starting to worry that they wouldn't have enough gas to reach the next town. "Come on, let's get some dinner."
Since it's Castiel's money, Dean decides he's the one who should pick where to eat, figuring that Cas will pick a burger place because he's got an addiction to cheeseburgers. Instead Cas takes them to a small Italian restaurant that does homemade cooking. It's way fancier than what Dean is used to, but they can afford it and Cas is beaming at him and Dean sees no reason why they shouldn't be here.
The waitress takes them to a corner table covered with a checkered red-and-white tablecloth and sets a candle between them. "I hope you'll enjoy your evening," she tells them, and that's when Dean realizes what it must look like and why they shouldn't have chosen this place.
He's about to tell her that this is not a date, this is most definitely not a date, but Cas smiles and thanks her and she winks in return, and Dean buries his face into the menu and tries to make himself invisible.
"I'll have the spaghetti bolognese with meatballs," Castiel tells the waitress. "Dean? What about you?"
Dean is too busy with his private freakout to read the words floating in front of his eyes. "Er, the same for me," he manages.
"Good choice, very Lady and the Tramp," the girl says, jotting down the order, and Dean groans. He's never getting this one's number.
Castiel frowns. "Dean," he says after she's gone to deliver their order, "what's Lady and the Tramp?"
"It's a cartoon," Dean explains. "About two dogs." He's most definitely not going to mention that the two dogs are in love. Cas is still not getting the reference, so Dean racks his memory. "There's this scene where the two dogs go to the restaurant and they get spaghetti with meatballs," he says.
"I don't understand," Cas says. "How can dogs order food?"
Dean isn't sure either, but then again he's only seen the cartoon once or twice, years ago when Sammy was still very little. He shrugs. "I don't know, they just do. And then their waiter sings some song and they kiss, except they're dogs so it's not a kiss, they just bump their noses together."
Then he realizes what he's just said and gets flustered again, except this time he doesn't even have a menu to hide behind, so he pretends to be fascinated by the pattern on the tablecloth.
"Is that how dogs kiss?" Castiel asks.
"I don't know, dude," Dean mumbles. "It's just a stupid kids' cartoon."
It feels as if the waitress takes forever to get back with their food. Thankfully she doesn't break out into song and doesn't make any more Disney remarks, she just sets the food in front of them and says she hopes it's to their taste.
The spaghetti are actually very good, though maybe it's because Dean is so used to greasy diner food that anything else tastes good by comparison. Still, he wolves it down and forgets all about fictional dogs.
Castiel seems to have problems with the spaghetti. "They're good, but very hard to eat," he says, sucking on a particularly long piece of pasta that leaves a smear of sauce at the corner of his mouth.