Summary: Sam sets Dean up on a blind date, but nothing is quite what it seems.
Tags/Warnings: Destiel, modern AU(? IDK what to call it), fluff, mechanic!Dean, accountant!Castiel, no beta we die like men
A/N: Alright, writing something a little out of my SPN wheelhouse but back into territory I used to always write! Saw this post by @colorlessjay and inspiration just hit. Whatever’s in your coffee, keep it up (and share with me, please!). Hopefully I did your idea justice! Thanks for sharing it 💜 (Also, please forgive me if Castiel is mischaracterized. I’m still in the early seasons of Cas)
It was a stupid bet.
Not because he was opposed to a blind date. But because Sam was throwing away money, and Dean was all too happy to abuse the hell out of a free meal. And some post-date sex too, if he was lucky.
The restaurant he pulled up to was far too swanky for Dean’s liking, and the two cars he parked his Impala between were worth more than yearly rent. He tapped his fingers nervously against the steering wheel and tugged at his collar, wishing Sam would’ve given him a bit more of a warning about the restaurant he had picked for Dean.
This was upscale. Like, way upscale. The kind of fancy where they probably had fifteen different forks and expected you to know which one to use first. The valet had given him a once-over when Dean had insisted on parking Baby himself, their eyes raised in silent judgement at Dean’s apparel. His second-best flannel and jeans with only a single tear at the knee were hardly the appropriate attire for this place. But it was too late to back out now.
“Fuck it,” Dean muttered, checking his watch – 6:55. Five minutes to spare. He was early, which never happened. Sam would’ve had a field day with that information. But knowing Dean’s luck, the person Sam had set him up with was probably already there, wondering if they had been stood up. Dean cracked his knuckles and gave his reflection a quick once-over in the rearview mirror before climbing out of the car, his usual bravado and swagger in place. It was a good thing Dean was used to faking like he belonged.
The interior of the restaurant was all polished wood and low lighting with a live jazz band playing in the corner.
“Reservation?” the hostess asked, her smile professional and polite even as she looked him over.
“Yeah, should be under Cas.” Dean shifted his weight from foot to foot uncomfortable. Sam hadn’t even told him his date’s full name, just that they had “similar tastes” and “would get along.” Knowing Sam, she was going to be some bookworm who’d spend the whole night talking about nerd stuff.
The hostess lead him into the restaurant, weaving between tables of laughing couples and groups of friends. Dean tugged at his flannel again and silently cursed Sam.
“Your party is already seated,” she said, stopping at a corner table.
Dean paused mid-step.
A man was seated there.
Not a woman.
A man.
This had to be a mistake. Or more likely, this was Sam’s idea of a joke. Set Dean up with a dude, take photos from the outside, and laugh about it for months. Classic Sam. The hostess cleared her throat. “Sir?”
“Uh, yeah. Thanks,” Dean mumbled, approaching the table. He was going to kill his brother. Slowly and painfully. Possibly with one of those fancy forks. Okay, kill was a little extreme. Maybe some Nair in Sam’s shampoo again would be enough. Or supergluing his laptop shut.
The man looked up, startled by Dean’s arrival, and holy shit – those were some blue eyes. Like, unnaturally blue. The kind of blue that put the sky to shame. They were striking, even in the dim restaurant lighting. The man tilted his head slightly, brow furrowing in confusion. His dark hair was tousled, like he’d run his hands through it a few too many times and somehow managed to make it look intentionally messy. He wore a crisp, button-down with a tie that matched his eyes, a stark contrast to the rumpled trench coat that pooled in his seat. Despite that, he was still better dressed than Dean.
“Can I help you?” he asked, his voice unexpectedly deep and gravelly. Dean sank into his chair across from the stranger and swallowed hard.
“Look, man, I know what’s going on. Sammy put you up to this? I gotta say, it’s a good one. He really went all out.”
The man’s confused expression only deepened.
“I’m sorry, but I don’t know any ‘Sammy.’” He glanced around as though he were looking for the parent of a lost child. “I believe you may have the wrong table.” Dean’s eyes narrowed at him. The man was certainly committed to the bit, he’d give him that.
“Right. So you just happen to have a reservation under the same name as my blind date? Come on, man. You’ve gotta do better than that.”
The stranger’s shoulders tensed.
“I wasn’t aware I was occupying someone else’s reservation. The hostess seated me here ten minutes ago.”
“Look, you can drop the act. I know Sam set this whole thing up to mess with me.” Dean scowled and leaned forward, lowering his voice. “What’d he promise you? Free drinks? Dinner?” The other man’s expression shifted from confusion to annoyance, and he pinched the bridge of his nose.
“Listen,” the man began, his voice dropping to a dangerous rumble. “I don’t know who you are or who this ‘Sammy’ is, but I have had too long of a week to be dealing with this. I simply want a quiet dinner. I’m not part of whatever game you think you’re playing.”
Dean’s certainly wavered. The guy seemed genuinely irritated, and as Dean studied his face, there was no hint of recognition there. No smug little smile that would give away the joke. Either this guy was an Oscar-worthy actor, or Dean had just made a complete ass of himself.
“Wait, so you’re not… Cas?”
“I am Castiel. Or Cas, as some call me,” he confirmed. “But I am certainly not your blind date.”
Dean ran a hand down his face, suddenly feeling like the world’s biggest idiot.
“So you’re not here because my brother set us up?”
“No,” Castiel replied firmly, his annoyance clear in the way his mouth formed a tight line. “I’m here because I wanted to treat myself to a nice dinner after a particularly rough week.” Then, as if the universe were laughing at him, the waitress appeared at their table, her friendly smile faltering slightly as she immediately picked up on the tension.
“Are you gentlemen ready to order, or should I give you a few more minutes?”
“Actually,” Dean began, already pushing his chair back, “there’s been a misunderstanding–”
“Wait,” Castiel said, and he seemed as though he were a little surprised at himself. Something about the embarrassed flush creeping up the stranger’s neck made Dean pause. The waitress slipped away. “I... believe we both may be the victims of circumstance. You were expecting someone named Cas for a blind date, and I happened to be a Cas who was seated at your table. Since you’re already here, you might as well sit back down. No sense in both of us eating alone.”
Dean hesitated, hand still gripping the back of the chair. This wasn’t how this blind date was supposed to go. Then again... Sam would laugh his ass off if Dean came crawling back home with his tail between his legs. The thought of his brother’s smug expression was enough to make Dean sink back into his seat.
“Yeah, okay. Thanks.” He cleared his throat. “I’m Dean, by the way. Dean Winchester.”
“Castiel Novak,” the man replied, holding his hand out over the table. Dean took it, surprised at the firm grip and rough feeling of calluses on Castiel’s palm. He had expected soft hands from someone who dined alone at a place like this.
The waitress returned with a smile that seemed to touch her eyes this time when she noticed that the awkwardness had dissipated.
“Have you decided what you’d like to order?” she asked, pen and paper at the ready.
“I’ll have the bourbon-glazed steak, medium rare,” Castiel said, closing his menu. Dean cracked open his own menu, eyes going wide at the prices. Oh, he was definitely making Sam pay for this.
“Uh, I’ll have the same.” He doubted this place had any burgers. “And a whiskey would be great.”
When she walked off, Dean drummed his fingers on the table, suddenly struck by a distinct lack of words. Blind dates were usually never awkward for Dean. All he had to do was lay the charm on the gal across from him, and things just went from there. But this? This was uncharted territory.
“So...” Dean started, “bad week, huh?”
Castiel sighed, and Dean could see the way the weight of the week pushed on Castiel’s shoulders.
“You could say that. I’m a tax accountant, and April 15th is three days away.” Dean grimaced, suddenly remembering that he needed to bother Sam about his taxes for the year.
“Tax day. That’s rough.”
“Especially when people who have known about the filing deadline for years still act surprised when it arrives,” Castiel said dryly. Dean tried not to look guilty at that. “How about you? What do you do when you’re not crashing a stranger’s dinner?”
Dean chuckled, feeling himself relax slightly. Maybe this wouldn’t be as awful as he thought.
“I’m a mechanic. I co-own a garage with my uncle. Not as fancy as number-crunching, but I’m good with my hands.” Dean immediately regretted his choice of words, feeling heat creep up his neck. “With cars, I mean. I’m good with cars.” Castiel’s lips quirked up slightly, the first hint of a smile Dean had seen from him.
“I imagine both skills come in handy.”
Their drinks arrived. A whiskey – neat – for Dean and a red wine for Castiel. He must’ve ordered it before Dean sat down. Dean took a healthy swig of his drink, the familiar burn putting him back into safer territory.
“So this... Sammy,” Castiel said, taking a careful sip of his wine. “Your brother, I assume?”
“Yeah,” Dean nodded. “Little brother that’s not so little. Guy’s a sasquatch. Stanford law and everything.”
“And he often sets you up on blind dates?”
“No,” Dean snorted. “This was a first. I usually do just fine on my own.” He paused, realizing how that sounded, then added, “I mean... not that I’m... well, you know.”
“I don’t actually,” Castiel said, his head tilting slightly. “But I’ll take your word for it.”
There was something disarming about Castiel’s direct gaze. It wasn’t judgemental or mocking, just... interested. Dean wasn’t used to being studied so intently. To someone who seemed to actually hear every word he said. If he was being honest, he wasn’t used to people not swooning. Not that he wanted Cas to swoon. Not that he would mind. That thought dredged up a weird feeling that Dean didn’t feel like grappling in the moment. In fact, he’d be happy if he never had to confront that at all.
Their steaks arrived, perfectly seared and glistening with the bourbon glaze. Dean cut into his, letting out an appreciative sigh at the first bite.
“Damn, that’s good,” he said, momentarily forgetting his manners. “Sam may be a pain in my ass, but at least he picked a decent restaurant.” Castiel nodded in agreement, savoring his own bite with closed eyes.
“I’ve been coming here on particularly difficult days for years. They have a honey cake that I find... comforting.”
“You come to a place like this for comfort food?” Dean asked, making a vague motion to the crystal glasses and linen tablecloths.
“Everyone’s definition of comfort is different,” Castiel replied. “What’s yours?”
Dean’s knife paused mid-cut, and he actually had to stop and think about it for longer than a moment.
“I guess my mom’s apple pie. Nothing fancy, just... home.” Dean hadn’t meant to reveal something so personal to a stranger, but something about Castiel made him easy to talk to. The two of them fell into a surprisingly comfortable silence as they ate. Dean found himself stealing glances at Castiel between bites. The guy was good-looking in an unconventional way. Perpetually rumbled but somehow still put together with that intense stare that seemed to see right through Dean’s usual bravado. It was unnerving. But not in a bad way?
“So, no date tonight for you either?” Dean asked, pushing his empty plate away. Castiel dabbed at his mouth with the cloth napkin.
“No. My social calendar is rather sparse these days. Work takes up most of my time.”
“All work and no play makes Cas a dull boy,” Dean quipped. He mentally facepalmed. “Sorry, that was–”
“Accurate,” Castiel cut in, a self-deprecating smile tugging at his lips. “My brother Gabriel tells me the same thing. Though he uses considerably more colorful language.”
“Younger?”
“Older, actually. Though you’d be forgiven for thinking otherwise considering his behavior.” Castiel shook his head. “He once filled my office with live ducks because he thought I was ‘quacking’ under pressure.”
Dean just about choked on his drink. Maybe it was Castiel’s dry delivery of the line. Or maybe it was the mental image of Castiel sitting at his desk with ducks waddling around the office. Either way, Dean laughed, deep and genuine.
“No way. Like actual ducks?”
“Twelve of them,” Castiel confirmed, his eyes crinkling at the corners as he smiled. “It took maintenance three days to repair the damage, and I’m still finding feathers in my filing cabinets.”
“Sounds like our brothers would get along. Sam once filled my car with packing peanuts while I was sleeping. Took me a week to get them all out.”
“And yet you still love him.”
“Well, yeah,” Dean shrugged, trying to come off as unbothered as possible. “Family, right?”
The waitress came by again.
“Can I interest either of you in dessert?” Dean glanced at Castiel expectantly.
“You said something about a honey cake?”
“Yes.” Castiel nodded, his expression brightening.
“Two honey cakes, please,” Dean said, the words surprising himself. He typically didn’t care for cake, but the way that Castiel’s face lit up had Dean curious. Must’ve been pretty good to get a tax guy excited.
When she left, a blanket of awkwardness settled over the table again. The impromptu blind-date-turned-friendly-dinner was coming to a close, and Dean found himself oddly reluctant to let it end. Dean cleared his throat.
“So, your original date. What happened there?” Castiel blinked and tilted his head again.
“I didn’t have one. As I said before, I merely wanted to treat myself to dinner.”
“Right,” Dean nodded, mentally kicking himself. “Sorry, I just assumed. Because it’s Friday night, and this place is...”
“Romantic?” Castiel offered, glancing around at the couples holding hands and the soft lighting designed to flatter features.
“Yeah.”
“I suppose it is. I never really noticed. What about your date? The real Cas?”
“I dunno,” Dean said with a shrug. “Sam’s the one who was in contact with her.” Dean grimaced, realizing that he hadn’t paid much attention to his surroundings during his meal. Poor gal probably showed up, couldn’t find him, assumed he stood her up, then blown up Sam’s phone. Oops. He actually felt a little bad about that.
The honey cake arrived, and as Castiel’s eyes lit up as he took his first bite, Dean found himself more interested in Castiel’s reaction than trying his own dessert.
“You weren’t kidding about this cake,” Dean said when he finally dug into his own. It was surprisingly good. Not too sweet, and the sliced almonds on top added just the right texture. “This might be the best dessert I’ve ever had. And I’m more of a pie guy, usually.”
“Don’t let Gabriel hear you say that,” Castiel replied with a small smile. “He owns a bakery that specializes in pies. He insists they’re superior to all other desserts.”
“Smart man.” Dean took another bite. “Though I guess I’ll have to make an exception for this cake.”
And just like that, the two of them fell back into a comfortable conversation as they finished their desserts, sharing stories about their brothers and work. Dean found himself laughing more than he had in months, surprised by Castiel’s dry humor that showed up once he relaxed. When the check arrived, Dean instinctively reached for it.
“I’ve got it,” Castiel said, his hand brushing against Dean’s as he also reached for the leather folder.
“No way, man,” Dean insisted, tugging the check closer to him. “This was supposed to be my treat. Well, technically Sam’s treat since he got me into this mess.” Castiel hesitated.
“You’re going to pay for dinner with a stranger who wasn’t even your intended date?”
“Hey, this turned out better than whatever Sam probably had planned.” Dean shot Castiel a grin. “Consider it my apology for crashing your solo dinner.” A beat passed between them before Castiel’s grip on the check loosened, and he relented.
“Very well. But next time, it’s my treat.”
Next time.
The two of them paused as the implication of next time hung between them, heavy but not entirely unwelcomed. Dean tucked Sam’s card into the folder and passed it off to the waitress, doing his best to ignore the strange flutter of something in his chest.
“So,” Dean leaned back in his chair, leg bouncing anxiously. “I’m supposed to report back to Sam about how this all went.” Castiel raised an eyebrow at him.
“Are you planning on telling him about our... misunderstanding?”
“Oh hell yeah,” Dean laughed. “This is too good not to. But I can’t help but wonder what the person I was supposed to meet would’ve been like.”
Castiel’s expression shifted slightly, something unnamable passing across his features before he neatly tucked it away.
“Well, I hope she would’ve been worth your time.”
“Honestly?” Dean shrugged. “I doubt she could’ve made tonight any better.” A hint of color touched Castiel’s cheeks as he glanced down at his empty dessert plate. The waitress returned with the receipt, and Dean signed it with a flourish, making sure to leave a generous tip.
“Thank you for dinner, Dean,” Castiel said, rising from his chair. “It was unexpected. But pleasant.”
“Yeah, same here,” Dean replied, standing as well. The two of them walked toward the exit together, shoulders occasionally brushing in the narrow path between tables. Outside, the night air was cool and crisp, a welcome change from the warmth of the restaurant. The sky was clear, but with all the light pollution from the city, the stars were barely visible. Dean hesitated at the bottom of the restaurant steps.
“Hey, you, uh... got a card?” he asked. “In case I need a tax guy?” he added quickly. Castiel’s expression softened, and he reached into the pocket of his trenchcoat before producing a business card.
“My work number is on here. But you can find my personal cell on the back.” He handed it to Dean, their fingers briefly brushing past each other. Dean took the card and flipped it over to see the neat handwriting. Castiel Novak, CPA. He smiled and tucked it into his own pocket.
“CPA,” Dean repeated. “Sounds official.”
“It is,” Castiel replied, the corner of his mouth quirking up in a half-smile. “I even have a special calculator and everything.” Dean laughed. Another awkward silence.
“So,” Dean finally began, rocking back on his heels. “Guess I should let you get home. Long day and all that.”
“Yes, I suppose so.” Castiel looked up at the night sky then back at Dean, a soft, genuine smile gracing his features. He took a half-step back. “Give me a call if you need help with taxes.” A pause. “Or a next time.” And with that, the two parted ways.
Dean slid into Baby’s front seat, still reeling over the evening. What the hell was that? He typed a message to Sam, his leg bouncing as his fingers tapped against the screen.
Sam’s phone pinged. Two notifications.
The first was from his bank, notifying him that his card had been used.
The second, a message from Dean.
Jokes on you. I ain’t paying you shit.
Sam typed a response back, frowning. He had been so confident about this gal.
Damn, and here I thought Cassie’s love for Led Zeppelin would’ve gotten you.
Three dots appeared, signifying that Dean was typing. Then they disappeared. Then they popped up again. Then, a text.
WHO?!
---
Likes, reblogs, and comments are greatly appreciated!
thinking about a scenario shortly after defeating chuck, pre-empty rescue. dean is in full widower mode, collapsing under the weight of grief, and sam is, as usual, prodding at him to open up.
sam’s cornered him in the kitchen, where dean went for more whiskey, because alcohol is the only thing that drowns out the constant drumbeat of you could have had me, you idiot, you could have had me, running through his head.
and sam is saying “i know how you feel, dean, but—” and it’s suddenly too much. something in dean just snaps.
he turns, only halfway facing sam. “you know how i feel? you knew jess for a year and a half, sam. i had cas for twelve. and from what i remember, you didn’t want to talk to me about her back then either. so leave it.”
sam, who was about to say “we both lost a friend, i cared about cas too, and he wouldn’t want us to stop living our lives”, just freezes, mouth open in shock.
dean pushes past him out of the room, and after about five minutes of stunned silence, sam thinks to himself well, i guess that explains why the strip club didn’t work last time.
i just think it's fun for dean to hear sam's sympathy and feel the overpowering urge to scream “what the hell do you know! you've never been married!' while simultaneously thinking “what the fuck is WRONG with me. I'VE never been married!” because now that he knows it was requited the whole time everything looks different in hindsight. he’s reinterpreting the last decade and especially the last few years and he has absolutely no clue how to handle it, because cas is gone.
It was the night of Halloween. Dean and Castiel were alone in the bunker, stuffing their faces with candy. They were well into several bottles of Whiskey, even Cas was slightly drunk.
“You know, there’s a myth that you can see your future husband in the mirror, if you eat an apple in front of it on Halloween night?” Cas asked out of nowhere.
“That’s stupid,” Dean replied.
“I wonder if it’s true.”
“It might. Wanna try?”
“I’m … Yeah why not? Do you have apples?”
“I think Sam went to the farmers market a few days ago an brought some …” Dean went to look for the apples in the kitchen.
“And I think we need a candle,” Cas shouted after him.
A few minutes later Dean came back with two exceptionally red apples and a black candle. They went to the men of letters washrooms and lit the candle in front of the mirror. It was completely dark in there except for the flickering light the candle provided.
Dean couldn’t help but shiver. Maybe it was the Whiskey talking, but if he squinted a little, he could already see blurry faces in the dim candlelight.
“Okay, you first,” he said, handing Cas one of the apples.
Cas cautiously went in front of the mirror, staring at it in his unblinking way, while gently nibbling on the apple.
After five minutes Dean couldn’t hold in any longer and impatiently asked, “And? Do you see someone?”
“I’m not sure,” Cas slowly answered, squinting even harder. “The only face I see is yours.”
“Let me try.” So Dean went in front of mirror, staring into it for several minutes, gnawing at his own apple. The candlelight produced dancing shadows which were intensified by the intense staring, but the only thing Dean could clearly see was Cas’ face.
“Move away a few steps, Cas,” Dean said, still concentrating on the staring and apple eating.
“Dean, there is no way you can see me from that angel. I made sure of it,” Castiel replied confused.
“Well … All I see is your face. So it doesn’t seem to be working,” Dean concluded, breaking eye contact with the mirror to look at Cas.
“why does this sound like a goodbye” insane response to a love confession from your best friend of 12 years. dean skips over any emotional vulnerability or reciprocation and immediately worries about cas’s safety. happiness has always been taken from him and this kind of happiness is SO monumental that the first thing dean can think of is “how soon is this going to be taken from me”
you see it’s funny because dean has no idea what he’s even agreeing to, and neither do we. so he literally looks at cas’s lips, softly (and kind of desperately) nods yes and after cas removes his hand, he fucking puckers his lips??? FOR WHAT???
WHAT WAS THE REASON?!!?
(also the way his eyelids soften up the tiniest bit while he puckers his lips in the last gif makes me want to throw something)
Your back to the future AU is my favorite thing on the internet!!!!!! I love it so much!!!! They are so sweet and funny. I love your art work and style!
♥️♥️♥️♥️
How do you think s6 Dean would react to seeing s16 Cas in a cowboy hat?
Probably like this:
Part 6 of "Back to the Future" AU
Castiel continues to be very very vague about who his husband is (spoiler: it's S16 Dean) and is trying so hard not to just outright laugh in Dean's face
Meanwhile, Dean is questioning a lot of things about himself. He doesn't think he can last any longer in the future, and he's no closer to figuring out where he's future self is (spoiler: S16 Dean is in the past)
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