A/N: Prompt posted by tumblr user DanglingThpider

Monday mornings are hectic at the Sioux Falls Gas N' Sip on the corner of Pine and Grove.

There's hardly a moment of rest between the cigarettes, lottery tickets, and gas receipts passed back and forth across the dinged up front counter, and Castiel, the lone sales associate, is almost too busy to notice that the constant swing of the store's front door, blowing the chilly October air inside, is making him shiver.

Almost.

His hands and arms are all but trembling by the time the line has finally dwindled, and Dean, the store manager, is suddenly swooping over his shoulder and pressing a too big jacket, emblazoned with the store logo, into his hands.

"Keep those things in the back for a reason, you know," he says good naturedly before shaking his head at Cas. "Can't have you going and getting sick on me now. Got to keep you sharp up here on the front lines."

"Of course," Cas smiles gratefully as he takes the jacket. "Thank you, Dean."

Dean grins and waves him off, but the small moment of kindness is well remembered a few hours later.

Cas has nearly finished restocking the dairy case when Dean taps him on the shoulder. He places the last gallon of chocolate milk into its spot before turning to Dean expectantly.

He knows, because he's been watching Dean fidget with his phone for the past twenty minutes, what he's about to be asked.

And, sure enough, Dean's going on a whole spiel about how he can never find a babysitter for Ben, his sweet but rambunctious three year old.

Castiel nods along, knowing it to be true. Dean has sheepishly asked him for his help a dozen or so times since Castiel first volunteered to help him out last May when Dean needed to go to a mandatory Gas N' Sip managers' meeting that was, inconveniently, scheduled on what was supposed to be his day off.

"Kid's a handful, you know? So it's hard to go out, even if it's just to help my brother's geeky ass bowling team meet their player quota. But, uh, Jo said she couldn't do it next Friday."

Castiel continues nodding. His brother Sam's bowling team competes, oddly, on Tuesdays the first and third week of the month and on Fridays the second and fourth. Dean, who is rarely able to go, has complained about its illogicality, on a number of occasions.

"So.. you're off tomorrow night, and, um, really hate to ask so last minute, but it's just... it's you, and, I know, God, I know, it's a Tuesday, but you...you free?"

Dean's hand is running manically through his hair, and he looks like he'll be devastated if Cas says 'no.'

Castiel squints at him. Dean's not usually quite this flustered when he asks for a favor.

Perhaps it has to do with Jo. "This is for more than just bowling?"

Dean breaks into a grin. "Uh, yeah, that's, uh, that's what I'm hoping."

Castiel sighs, and Dean's grin falls.

Cas, deciding that he may as well forego his plans of curling up to watch the latest Dr. Sexy for the sake of Dean's love life, dredges up a false smile of his own. It's not as though Dean is magically going to decide to ask him out anyway. "I would be happy to help out you and Sam's bowling team."

Dean looks dazed for a moment, like he really hadn't been expecting Cas to say 'yes,' then he simply beams at him.

He must really like Jo.

"Awesome."

XXX

"I don't know how he was weird about it, Sam. He just was. And, it's Cas. He's weird about a lot of things. You think, maybe, he doesn't like bowling?"

"Well, it's kind of a weird first date. You've known him for months, Dean. Think you could do something more intimate than a bowling game with people he doesn't even know."

"Uh...he knows you."

"Barely. I've met him like twice," Sam says. "Seriously, you're playing this way too safe. Go out to dinner or something."

Dean sets down the sponge he's been fruitlessly scrubbing at a used casserole dish with and pinches at his forehead. "What about your team?"

"It's a bowling league, Dean. The world's not going to end if we're short a few guys. It happens."

"Yeah, okay. Uh, I got to go... Ben's, uh.. Ben!" Dean drops the phone on the counter before tugging Ben, who has somehow managed to climb up three shelves already, out of the refrigerator. "Ben! No scaling Mount Leftover. Get down!"

XXX

By the time Castiel is clocking out the next day, babysitting Ben is roughly last on the list of things he wants to do.

It just sounds exhausting.

It's been one of those days - the kind that starts with an overslept alarm, a missing roll of toilet paper, and a set of car keys that aren't anywhere he remembers putting them.

The kind that continues with a customer who doesn't understand why the price of gas is twenty cents higher than it was yesterday and spends thirty minutes arguing the point before demanding to speak to a manager, with a slushie machine that dies after half its contents leak onto the floor, and with a supply order, filled with all the most popular flavors of soda, that doesn't show up. And so on.

At the end of it, all Castiel wants to do is go home.

Instead, he has a promise to keep.

So, with a weary sigh, he has Garth, one of the other sales associates, ring up trail mix, a miniature apple pie, and a toy car for him before he heads out the back door, without even bothering to take off his employee vest.

A little of his frustration melts, when he gets to Dean's, and Ben runs up and hugs him around his legs, shouting, "Cas here, Daddy! Cas here!"

Because, as trying as watching him can be, Cas really likes Ben, if only a little because Ben really likes him.

"Yeah, kiddo, I can see that," Dean says before grabbing the bag out of Cas' hands and rooting through it. "Man, I'd say you shouldn't have, but, dude, always, always bring me pie."

He then pulls the packaging off the toy car and hands it to Ben. "And what do you say?"

"Cas rocks," Ben says with a lopsided thumbs up before focusing all of his attention on his new toy - Cas, Dean, and the new girl striding into the living room entirely forgotten.

"So this is Cas, huh?" the girl, who Cas presumes is Jo, asks. "About time we met with how much this guy goes on about you."

She jabs her thumb at Dean, and Castiel tries to remember what, if anything, he has heard about her.

He comes up blank. "He has not 'gone on' about you?"

Jo snorts before punching Dean's shoulder. "You embarrassed by me or something?"

Dean shrugs. "Haven't rubbed you out of the family tree yet."

"I'm not even on the family tree," Jo says.

Castiel frowns, feeling that he is missing something vital here, but he can't quite place his finger on what.

"So, Cas, this is Jo," Dean says, gesturing vaguely in her direction. "Really haven't told you about her?"

"You have not."

"Jo's my kid sister," Dean says, then elaborates, unhelpfully, "well, kind of my kid sister."

Cas blinks, certain he has misheard. If Jo is Dean's sister...then...

"Stepsister, or will be, if Mom and Bobby ever manage to tie the knot," Jo mutters before turning her eyes appraisingly over Cas' outfit. "So, Cas, you wear your Gas N' Sip get up on all your dates or is Dean just special?"

Then...

"My date?" Cas hears himself ask. He's not sure he remembers actually forming the question, as it would imply that not only has Dean Winchester already asked him on a date, he's already agreed to go on it.

Tonight.

This is not, per se, a bad thing. In fact, quite the opposite. Cas knows this.

But the knot his stomach is twisting into, as he realizes that he is still wearing his work clothes and is expected, in the imminent future, to mingle with complete strangers at a bowling alley, has not gotten the memo.

"Whoa, Cas, you okay?" Dean asks as he places a hand on his shoulder. "You're looking kind of green."

"I, uh, I think I'm going to be sick. If you'll excuse me."

Ten minutes later, when has not emerged from it, Dean is knocking hesitantly on the door to the bathroom. "Uh, Cas, you okay in there?"

Cas splashes a little more water on his face before slowly opening the door, and offers, in response to Dean's unasked question,"I thought Jo was your date."

Dean side-eyes him, obviously still confused. "And you were...?"

"Babysitting."

"Oh." Comprehension dawns all over Dean's face before being replaced by a look of dejection. "Been turned down before. But, man, throwing up on me? That's cold."

"Dean, I would very much like to go on a date with you."

"But you..."

Cas puts his hand up to stop Dean's clearly self-deprecating train of thought. "But I was unprepared and overwhelmed by this pleasant turn of events."

After a moment's contemplation, he adds, wearily, "But I am still unprepared for bowling."

"Yeah, you don't look like you're really up for anything," Dean says as he gestures for Cas to follow him down the hall. "Come on, got a Sprite with your name on it out in the kitchen. And after you drink it, can take you home, if you want, or, uh, we can keep tonight low key. Uh, stay on the couch, order a pizza, watch Dr. Sexy. Something."

Dean's giving him that look again, the hopeful flustered one. It's less pronounced than it was the day before, but it's still there.

Cas regards him with fond amusement. "Dean, I've already said 'yes.'"

"Then, come on," Dean smirks at him. "Lose the vest. Stay awhile."