The next week, Sam gets up the guts to ask Jess out. She, of course, accepts and they set a date for that weekend.
About an hour before the date, Dean finds Sam in his bedroom surveying his face in the mirror. "Dean, do you think I need to shave?" he asks.
Dean snickers from behind him, leaning his weight against the door jamb and folding his arms over his chest. "What’s there to shave?" he asks.
Sam rolls his eyes and turns to face his brother.
"You nervous?" Dean asks.
Sam nods.
"Don't be," Dean tells him. "You're gonna be fine."
Sam nods again. "What was your and Cas' first date like?" he asks.
"Oh, um," Dean's mind blanks as he realizes technically this will be their first date. Even if it is a fake one. "A lot like this, I guess. You know, I was totally awesome, he was a little bit nervous, but it all worked out."
"Did he shave for you?"
Dean thinks about the few times he's seen Castiel with scruff and smiles. "Nah, I kinda like him with a little bit of peach fuzz," he says.
"Did you guys hold hands?"
"Yep."
"Did you guys kiss?"
Dean quirks a smirk at his younger brother. "Definitely. Cas couldn't keep his hands off of me," he says.
"Ew, Dean! That's gross!" Sam's face is all scrunched and personally wronged, but Dean just chuckles.
"You asked!" Dean counters.
~
When they pick Jess up, Dean doesn't even have to tell Sam to get out and go to the door. Dean and Castiel watch out the window as Sam shifts on his feet, waiting for Jess to answer the door.
"He seems nervous," Castiel points out.
Dean lets out a laugh. "He's terrified!"
Sam walks Jess down the path with their arms linked together and opens the door for her like the perfect gentleman Dean's always taught him to be.
Jess greets Dean and Castiel as she slides into the back seat and Dean shoots her a smile in the rear view mirror. "Okay," he says, "everybody ready?"
"Where are we going?" Jess asks as Dean pulls away from the curb.
"Oh, Sam didn't tell you? I let him pick the place, hope you're okay with Chuck-E-Cheese!" Dean answers enthusiastically.
Sam groans from the back seat, and Castiel shoots Dean an amused smile.
They go to an old bowling alley downtown that's hosting black light lanes all night. The place is lit up with neon and swimming with teenagers enjoying their first weekend of summer break.
As they shoulder their way through the dark, Castiel runs smack dab into the hip of a girl shooting pool with a bunch of guys. When she turns around, Castiel opens his mouth to apologize, but Dean cuts him off when he sees who it is.
"Pamela?"
"Dean Winchester," Pamela says with a smirk. "I haven't seen you in ages."
"You back for the summer?" Dean wonders. He waves Sam along to pay for their lanes, but presses his shoulder against Castiel's in hopes it will make his best friend stay. It does.
"Sure am, got back yesterday! What about you?"
Dean nods and Pamela's eyes flick to Castiel. "And who's this pretty little thing?" Pamela asks.
Castiel's face pulls into a scowl that causes Dean to shake his head and laugh. "This is my boyfriend, Cas," he says putting an arm around Castiel's shoulders. He's finding more and more that Castiel is increasingly compliant when Dean is touching him in one way or another.
"Nice to meet you, Cas. I'm Pamela."
Castiel offers Pamela a curt nod. "Hello, Pamela."
"So listen, a couple of friends are meeting down at Southern Comfort in a few hours. You guys should come--we can catch up, all that good stuff." Pamela flashes Dean a wide smile and her teeth glow beneath the black lights.
"I'll have to check with Sam," Dean states. "We're kind of chaperoning his first date."
"How adorable," Pamela drawls.
"You know who you should give a call though is Charlie. I bet she'd love to hear from you."
"Oh, Red Queen! I miss that girl."
"Like I said," Dean says with a knowing gleam in his eye, "give her a call."
From behind them one of the guys Pamela is with nudges at her shoulder with his pool stick. "It's your turn, Barnes," he says.
"I'll see you boys later, okay?"
"Call Charlie," Dean prods again. Pamela offers them both a wink, and then she's turning back to her game while Dean leads Castiel to where Sam and Jess are lacing up their bowling shoes.
"You certainly know a lot of women," Castiel points out as they walk, their shoulders brushing amiably.
"What can I say?" Dean asks. "The women love me."
The four of them decide to split up into two teams, couple against couple and as Sam sets up their names on the computer, Dean slides into the chair next to Castiel. Castiel is bent over, trading his street shoes for bowling shoes, but when he sits up Dean asks, "You any good at bowling, babe?"
"I've never bowled before," he confesses, and Dean gawks at him for a good few seconds before offering Castiel a grin.
"Well, you'd never played Super Mario Kart either, and you won the whole fucking thing," he points out.
Castiel seems to mull this over before nodding and saying, "That is true."
"Yeah, see? So we'll still kick their asses. Besides, I've always been pretty good with balls." Dean wiggles his eyebrows at Castiel who huffs at him with a shake of his head before Dean tugs Castiel over to pick out a ball.
Before the game gets started, Dean walks Castiel down their lane, showing him the arrows on the floor and explaining how to aim. "Your bowl should all be one fluid movement," Dean states.
They stop at the line, and Dean places his hands on Castiel's shoulders, standing behind him and positioning Castiel like he's just about to toss his ball.
"Shoulders loose," Dean says, "that's it." He wraps a hand around Castiel's waist, resting his palm on Cas' belly and taking Castiel's right hand in his.
"Pull back--" Dean pulls their arms back as if there were a ball there “--and when you swing forward, that's when you let go of the ball."
Dean's well aware that Castiel could probably grasp the concept just by watching other bowlers, but if they really were dating Dean would take every opportunity he could get to have his hands all over Castiel, and because he knows Sam and Jess are watching, he does just that. But only because they're being watched, of course.
"Any questions?" Dean asks.
When Castiel speaks his voice comes out rough and strained, "No, I think I understand."
"Awesome." Dean drops his hands and leads Castiel back to their chairs, and without any further ado, they begin to bowl.
As it turns out, Castiel is much better at Super Mario Kart than he is at bowling. His first several balls go straight for the gutter, and the rest tilt off to the side right before hitting any pins. He gets progressively frustrated throughout the night, which Dean finds downright fucking adorable, and after Castiel's last frame, he retreats back to their chairs with shoulders hunched in irritation and a scowl on his face.
"I do not like bowling," he tells Dean.
Dean looks up at him from where he sits in his chair and smiles at Castiel. "Finally found something you aren't good at, huh?" he asks.
"I'm terrible," Castiel grumbles.
Dean reaches out and slips his fingers into one of Castiel's belt loops, pulling him in and then down onto Dean's lap. Castiel falls gracefully and looks down at Dean through his lashes as Dean wraps his arms around Castiel's waist.
"You may have been terrible," Dean says, "but I sure did have fun watching you try."
The frown on Castiel's face softens ever so slightly and after staring at Dean for a moment he bends and presses his lips against Dean's cheek. It's a soft touch, barely there and quick, but as it happens, it feels like the world slows down and fades away until there's nothing left but Castiel and Dean.
Dean isn't sure when the hell he turned into such a sap, getting all flustered over a kiss on the cheek, but, if this is what it feels like to be into the mushy feelings crap, then he sure as fuck is on board.
The moment is broken when Sam shouts to Dean that it's his turn. Castiel slides off of his lap almost regretfully, and Dean drops a kiss to his best friend's forehead before taking his turn.
In the end Dean and Castiel lose - turns out Jess is a wicked bowler - but Dean doesn't even give it a second thought as he turns in his bowling shoes, instead replaying in his mind Castiel fumbling with his bowling ball and scowling as it went a different direction than he intended. It had been a very entertaining night.
As they pile back into the Impala, Dean offers the idea of getting food at Southern Comfort. Sam and Jess agree, so Dean heads them in the direction of the diner, explaining to Castiel that Southern Comfort is where he and his guild spent a lot of nights after particularly successful raids.
As soon as they're outside the diner, the smell of grease and rich Southern foods hit Dean's nose, and his stomach growls. It's been far too long since he's had good Southern food, and if Dean is extra quick to get out of the car and herd everyone inside, well, he really can't be blamed for that now can he?
The interior of the diner hasn't changed a bit since Dean's last seen it. The decor is still tacky, the corner table he and his guild used to frequent is still worn and faded, but the food smells just as good as ever, and Benny's there, smile wide and eyes bright.
"Hey, brother," Benny greets, pulling Dean into a hug and thumping him on the back. "I heard you were back in town."
"Yeah," Dean says. "It's good to be back."
"This must be the boyfriend," Benny states, extending a hand to Castiel. His voice has a cool edge to it, but Dean brushes it off.
"Yeah, Benny, Cas. Cas, Benny."
If Dean thought Castiel was standoffish meeting the women in Dean's life, he's even more so with Benny. Castiel stares down at Benny's hand for what feels like a full minute before gripping it stiffly and pumping it once.
"Down boys," Dean mutters as he watches the icy exchange.
"Alright, well. I think you know where to go," Benny muses, smirking at Castiel and handing Dean some menus and gesturing towards the table that's already occupied with several of the people Dean used to game with.
"You gonna eat with us?" Dean questions, accepting the menus from Benny and grabbing Castiel's hand.
Benny eyes their hands, but doesn't say anything other than, "Yeah, just got some stuff to take care of first."
Sam steps in front of Dean, taking two menus from him and ushering Jess into a private booth for just the two of them. "We're gonna sit alone," he informs Dean.
"No making out, you two," Dean says, pointing his finger at Sam and then at Jess as he and Castiel pass them by.
Sam shakes his head.
At their table Castiel meets Aaron, who barely lifts his eyes from his phone long enough to offer Castiel an awkward salute, and Victor, who grumbles a hello before bitching about having to wait for everyone to arrive before he can eat.
Pamela arrives soon after that, punching Aaron on the shoulder as a greeting when he won't acknowledge her for longer than a couple of seconds.Charlie arrives a few minutes after Pamela, looking flustered when she approaches the table. Her eyes flit back and forth between the empty space next to Pamela and the empty space next to Castiel, but when Dean gestures with his eyes at Pamela and nods approvingly, Charlie dumps herself next to the other girl and nervously tucks a strand of hair behind her ear.
"Ladies and gents, I give you, the Red Queen," Pamela jokes as she wraps an arm around Charlie's shoulders and pulls her in to kiss her on the cheek.
Charlie blushes deeply and flutters her eyelashes. "It's good to be queen," she says.
Dean does his absolute best not to roll his eyes.
When Benny comes to take their order and Dean orders the Dean Burger, Castiel casts a glance at Dean. "They have a burger named after you?" he asks.
"Sure do," Benny pipes up. "Dean created the recipe."
"I'll have one of those," Castiel states, firm decisiveness in his voice.
"Sure you can handle it?" Benny asks, and Dean can practically feel the tension rolling off of his best friend and Benny in waves.
"Quite," Castiel confirms.
Benny nods and moves on to Victor.
"I didn't know you created recipes," Castiel tells Dean as the rest of the table orders. His eyes are soft, a fond sort of amusement there, and it makes Dean smile.
"It's not a big deal," he says with a shrug. "Benny and his family got sick of me making all sorts of special requests on my food, so they just told me to tell them what the hell I wanted and then named it after me."
"I'm sure you had more of a hand in it than that."
Dean thinks back to the time when he frequented Southern Comfort; late nights with Benny and the rest of the guild, getting hankerings for things that weren't on the menu that Benny and his family would whip up anyway. They had told him more times than once that he had a knack for food, but he'd always just brushed it off and countered with, "I have a knack for eating."
"Nah," Dean finally responds, offering Castiel a wide grin. "I just like to eat."
Castiel quirks a smile, "That I did know."
Their food doesn't take long with no other patrons in the diner to hold things up.When Benny sets down a burger the size of a small animal in front of Castiel, a quiet determination steels Castiel's features and Dean throws his head back and laughs.
"Biggest burger we got," Benny tells Castiel with a sarcastic wink, and then he's serving the rest of the table and making Charlie scoot over so he can take a seat next to her.
The table falls into an easy conversation, joking about times past and catching up on where everyone is nowadays, and it feels just like old times again, but with the added bonus of having Castiel by his side.
Castiel finishes off his burger in record time and when his plate is cleaned, Dean asks him what he thought, to which Castiel offers him a lazy smile and says, "That made me very happy."
Dean can't help the smile that stretches across his face.
By the end of the night Dean is full and warm and ready to drop into bed, and, if Castiel's heavy head on his shoulder is anything to go by, he’s not the only one. When Sam comes over and informs Dean it's close to Jess' curfew, Dean knows it's time to call it a night.
He takes care of his and Castiel's check, says good bye, and leaves the diner for home.
When they finally reach the house, Castiel is like a dead man walking; his movements are sluggish, his eyes droopy, and if it weren't for Dean's arm around his waist, he may not have made it up the stairs alone.
The door to their bedroom is barely closed before Castiel is pulling his shirt over his head and fumbling with the button fly on his jeans.
"Whoa there, eager to get out of our clothes, are we?" Dean jokes.
"I'm very tired, Dean," Castiel states, like Dean is being entirely too dense for his patience at the moment.
Dean snickers at him and begins to remove his own clothing.
By the time Dean is in his pajamas Castiel is already in their bed, burrowing underneath the covers and laying more in Dean's spot than his own. Dean flicks the lights off and pads around to his side of the bed before sliding in next to his best friend.
"You gonna cuddle me again?" Dean asks as he turns on his side and Castiel wiggles closer to him, molding his body to Dean's and draping an arm over Dean's waist.
"I told you I like to be close to you," Castiel mumbles against Dean's back. "You're warm."
Dean pulls the covers over them and begins to settle in for the night. “Hey, what was up with you and Benny tonight?” he wonders.
“It appears neither of us likes to share you,” Castiel grumbles.
“There’s plenty of me to go around,” Dean retorts, but he’s not even sure if Castiel heard him, his best friend's soft snores filling their room.
As Dean drifts off to sleep that night, his heart beating a happy tattoo against his chest with Castiel wrapped around him like it's something they've always done, Dean wonders if all best friends treat each other the way he and Castiel do.