Chapter Text
On September 8, 1982, the earliest prototype of the Boeing 767 operated its first flight, from Chicago to Denver. Three years later, another jet flew the same path. This 767-200 would turn out to be the most important object in pretty much Dean’s whole universe.
At six years old, he was fascinated by the sleek-looking aircraft, and so excited to fly. Even after his disastrous maiden voyage, to hear Mom tell it, you practically needed the jaws of life to pry him away from the windows at Denver International in Colorado, because he wanted to watch the takeoffs and landings. Though he’s never gotten over the terror of that first flight, never stepped foot on a plane again, it didn’t kill his interest in the slightest. If anything, the idea that seventy-five tons of airplane, plus the people on board, could be jettisoned into the air and stay there only added to his obsession. Despite being terrified of them, Dean just really fucking loves planes.
In high school, Dean was thrilled to discover that he had a knack for math and physics. He found a kind of beauty in aerodynamics and fluid mechanics; in the way that human beings can manipulate the world around them to force it to work for them, not against. Somehow he managed to pull in a full scholarship to MIT as a mature student, graduating with honors mere weeks before he lost his dad.
Much to his surprise, he also discovered a knack for drawing when he took tenth grade art to impress Lisa Braeden. He's spent a large portion of his free (and not-so-free) time since then doodling airplanes and their engines, for all the good it's done him. He's just putting the finishing touches on the tricycle landing gear of a 1963 Piper Colt, its Lycoming O-235 engine in an inset on the page, when his first customer of the evening walks in with a clunking, clanking sound.
The figure in the doorway turns back towards the sound, the end of his tan trenchcoat flaring as he does. Only a sliver of his profile is visible, but it looks like he’s squinting up at the cowbell above the door, and the drumstick Dean had rigged to hit it when the door opened. Taking the opportunity it provides, Dean clocks the rugged jaw, five o’clock shadow, and sharp cheekbone that’s just barely tipped towards him. In the slanting winter sun that shines from behind the man, Dean’s sure that he can see long lashes land on a rosy cheek when the stranger blinks. Still, none of it prepares him for what he sees when the man turns around.
All those features put together make quite possibly the most gorgeous man Dean’s ever laid his eyes on. Not wanting to be caught out staring, he quickly grabs a clean towel and a tumbler that’s already been dried, pretending to polish the glass. His papers get hidden beneath the stack of menus sitting to his left. He hears the cowbell sound again as the door closes, but doesn’t look up until he sees the feet of the approaching customer on the sticky floor across from the bar.
Sensible black boots, standing in a small puddle of melted snow, lead to navy blue trousers that flap around the ankles but hug a pair of thick thighs. A matching navy blazer covers a baggy white dress shirt, and it’s all topped off with that godawful fucking trench coat.
Dean forgets all about the man’s attire when he gets his first look up close.
Not only is his beauty otherworldly, his face is vaguely familiar. Despite his best efforts, Dean finds himself staring, caught like a deer in the headlights until he’s thwacked on the shoulder by a dish towel. He startles, not having noticed Ellen's approach, and there’s a definite chuckle that she can’t quite suppress as she addresses the new arrival.
“Pardon him, darlin’. He’s a sucker for a pair of blue eyes. Give ‘im a minute and he’ll reboot. In the meantime, what can I get for ya?”
“Wait, hold up,” Dean interjects before the man can give his order. “Cas?” Leaning on the bar, he tilts forward, squinting as if it’ll help his already perfect eyesight.
“Cas Novak, right? You were a couple years ahead of me. I remember thinking your goth/punk/whatever look was so badass.” Dean stops himself there before he rambles himself into confessing the giant crush he’d had on Cas for the entire two years they’d been in school together. The tips of his ears burn as he fights the blush from making its way to his cheeks.
Cas isn’t doing much better, pink sitting high on his glorious cheekbones.
“Thank you, I think,” he replies with the tiniest hint of a wry grin. “I’m happy to say those days are behind me now.”
“I don’t know, I think it would be better than whatever you’ve got going on there. You look like some kind of tax accountant.” As soon as the words are out, Dean wants to take them back. He’s horrified at himself, and so is Ellen by the wince he catches out of the corner of his eye.
Before he can apologize or backpedal, Cas huffs a small laugh, reaching into his inner breast pocket. “You’re not entirely wrong,” he tells Dean, handing over a simple, white business card. Engraved in black font reads ‘ Castiel Novak, Founder & CFO, Novak Aviation ’.
Dean’s heart stalls in his chest as he reads the card, mind instantly jumping to the nearly-full sketchbook in his bag with the realization that he’s shot himself in the foot by insulting the head of the biggest aerospace manufacturer on the entire planet. Somehow he hadn’t made the connection that the Cas he knew in high school and Castiel Novak of the aviation empire were one and the same.
“God, I am so sor –” Dean tries to say, shutting his mouth with an audible clack when Cas (Should he call him Castiel now?) raises a hand to stop him. He doesn’t look particularly upset but, who knows, maybe he has a great poker face.
“It’s alright, Dean,” Cas reassures him, “my brothers have said much worse to me about my outfit choices. Perhaps this is a sign I should listen to them.” He grimaces as though that prospect is particularly unappealing.
Eager to get that expression off of Cas’s face, Dean picks up the towel he’d dropped and tosses it over his shoulder. “So what’ll be, Cas? We’ve got the biggest liquor selection in Lawrence, and six different local beers.” He’s rewarded when Cas smiles again, still small but with less of an edge to it this time.
“I’ll have a beer, please. Whichever is your favorite.” Cas slips onto the stool directly across from him as Dean opens his beer.
Without even looking at the label, plush lips wrap around the rim of the bottle and Dean has to busy himself cutting more limes so he doesn't stare. Even so, he sees the bob of Cas’s throat as he drinks, swallowing reflexively at the sight. His mind is still reeling at the sight of his teenage crush here in Ellen’s bar, let alone the fact that he’s the reclusive founder of a billion-dollar aviation company. There’s no way he’ll be able to sit here and watch him drink Dean’s favorite beer – not like that .
Making some vague excuse about needing to check stock, Dean doesn’t hesitate to slip out around the end of the bar and through the door labeled ‘Employees Only’. He catches Ellen asking “So, you know Dean, do you?” but can’t hear Cas’s reply, muffled as it is by the door between them. The very same door Dean is now sliding down, to land on the floor with his back to the wood.
“Fuck, fuck, fuck .” Realistically, there’s no way Castiel Novak is going to look at Dean’s shitty drawings, and there’s sure as shit no way he’s gonna look at someone like Dean a second time. Sure, he’s technically a business owner, but he doesn’t think barely limping your late father’s floundering auto shop along can be considered anything near ‘successful’. As far as Cas knows, Dean’s just some lowly bartender, anyway. Teenage Dean pines fruitlessly in his chest, something he tries to shove down as best he can.
Taking a few, heaving gulps of air, Dean finally manages to calm himself enough that he thinks he can face going back out there. He peels himself off of the door, before bracing his hands on his thighs to leverage himself up. Though he’s only thirty-three, his knees creak like he’s eighty as he stands. Contempt briefly flows in John Winchester’s direction before Dean rearranges his expression to as neutral as he can and opens the door.
Several steps towards them, Dean registers what it is that Cas and Ellen have their heads bent over, animatedly discussing. He nearly turns around and walks right back out the door – the urge to disappear through the fire exit is strong. Cas looks up before he can make his move, however, his intense expression lightening as he catches sight of Dean. He beckons Dean over eagerly.
“Ellen tells me these are your drawings,” Cas says as he holds them up in the air between them.
Dean recognizes the top drawing, though it isn’t one of the ones he had hidden below the menus. This one should be tucked safely away in Dean’s sketchbook. A hot flash of anger burns through Dean at having his personal items shown to a virtual stranger. It’s quickly extinguished when he sees how excited Castiel looks. Nodding tentatively, he continues his approach, ending up beside Ellen and directly in front of Cas.
“Yeah, uh.” Dean clears his throat nervously as he takes the drawings from Cas with shaking hands. “Yeah, I dunno, I just like planes, and I like to draw them.” He shrugs as if it’s no big deal – because he’d rather it wasn’t a big deal. Sure, Cas might think his drawings are neat, because Cas likes planes, too, but he’s never going to be interested in Dean beyond that. People in Castiel’s position don’t look at bartenders as anything more than staff.
“Did you come up with this yourself?” Cas points to the rendering of a Lycoming O-360 engine that Dean had recently drawn. When Dean nods in affirmation, he watches as Castiel’s countenance brightens even more.
“Dean, this is brilliant, you have to know that. The modifications you’ve made are amazing, something I never would have thought to do. Is this for a plane of your own? Do you fly? Have you ever considered working in aviation?” His excitement is palpable, if a little overwhelming.
“Uhh, I –”
“I’m so sorry, Dean, that was too many questions at once. It’s just been a while since I’ve met anyone with as much potential as you have.”
Dean can hardly believe what he’s hearing. He spent so much of his life being discouraged from drawing, discouraged from wanting to do or be anything more than a grunt at a repair shop, that hearing praise is foreign to him. He looks around to see if anyone heard, but there’s no one else in the bar this early on a snowy day, and Ellen seems to have disappeared back to her office. Licking his lips nervously, he attempts to deflect instead of answering Castiel’s interrogation.
“Nah, man, I don’t fly. I did it once, and there was so much turbulence I was sure we were going to plummet out of the sky. Filled the barf bag and my mom’s purse before the flight was through. Never again. My sweet Baby can take me anywhere I need to go thanks to the Interstate system of these blessed United States.”
A strange look passes over Castiel’s face before he replies. “You know that flight is infinitely safer than road travel, do you not?”
“Maybe, but I’d much rather be the one behind the wheel, instead of trusting my life to someone else and fucking autopilot. ” Dean laughs as he says this, not wanting to truly offend Cas.
“So you’re a control freak.” One of those dark eyebrows arches upwards, nearly making Dean literally weak in the knees. He leans onto the bar to keep himself upright, not sure if he’s going to survive Cas being here in front of him for long.
“There you go putting words in my mouth,” Dean teases. Reaching to the cooler below the bar to grab another beer for Cas, he mutters to himself, “Could put something else in my mouth, if you wanted.” When he stands, Castiel’s eyes have widened, but he doesn’t say anything so Dean assumes he didn’t overhear.
Wanting to change the subject, Dean stashes his drawings under the bar top, committing to moving the ones under the menu as soon as Cas isn’t looking. “So, what have you been up to since you graduated?” he asks.
***
The conversation flows easily, the topic drifting from families, to how they ended up where they are, to what their New Year's resolutions will be. It's more than Dean has shared with anyone else, even Lisa. Around them, the bar starts filling up, and Dean is eventually called away to take another patron's order. The third time he comes back, Castiel is shrugging that ugly old coat over his shoulders, a look of regret on his face.
"I should go. I don't want you to feel like you need to cater to me. I should probably get some rest, anyway, I'm still pretty jetlagged."
The second part of his statement dries up the protests that sat on Dean's tongue. "Yeah, man, of course. Get back safe, okay?"
"I will." Castiel pauses, looking as if there's something more he wants to say.
Dean prays no one calls for him before he can say it. His eyes track Castiel's tongue where it darts out to wet his lips. Something about that seems to strengthen Castiel's resolve, and he steps back in closer to the bar.
"Dean, I will understand if you say no, but I would very much like the chance to get to know you more. Would you have dinner with me?"
Freezing, Dean once more resembles an animal in the high beams. The invitation is so unexpected that he’s having trouble coming up with an answer. A patron calls out for Dean, shaking him out of his stupor, and he nods vigorously. “Yeah, Cas. Yeah, I’d love to.” He’s sure he’s grinning like an idiot, but then, so is Cas.
With an awkward wave that Dean returns before turning to the next patron, Cas is on his way. Dean doesn’t see the moment he walks out the door, but he feels the weight of Castiel’s absence nonetheless.