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Good Luck, Babe.

Summary:

Castiel Novak has spent years loving Dean in the quiet spaces between what’s said and what isn’t. He’s learned to live on scraps – shared beds, secret touches. But after another night of giving too much and waking up to nothing, Cas finally draws the line. He can’t do this anymore. He doesn’t want to call it off, but if he won’t call it love, he’ll just go find someone else to call him baby. He's tired of opening his heart to someone who just sees him as an explicit kind of love affair.

Dean Winchester never meant to fall in love with his best friend. Sure, he can shoot another shot to try and stop the feeling, but Castiel has always been the one thing that feels real. Still, fear kept his mouth shut and his heart locked up – until he sees someone else’s hand on Cas, someone else leaning in to make him laugh. Jealousy simmers into something sharp and desperate because losing Cas? That would wreck him. But under the glitter and neon lights he’s suddenly standing in the face to face with "I told you so” and starting to realise he may already have.

Inspired by: Good luck, Babe! – Chappell Roan

Notes:

well... I never thought I'd start and finish a fic within a respectable time frame, but here we are! I love it when my ADHD decides that writing is my hyperfocus for the week!

This was originally going ot be one long ass one-shot, but I decided to break it down in the Character-centric POV chapters to make it easier for you all to follow. You're welcome.

(See the end of the work for more notes.)

Chapter 1: Castiel

Chapter Text

…::::::…

It's fine, it's cool
You can say that we are nothing, but you know the truth

…::::::…

 

He knew it was early when he roused from sleep; the pale grey of dawn leaked through the barely hanging blinds as the night before slowly came back to him. The wandering of hands, the feel of a warm mouth, fingers balled, tugging at the hair on his head as his name was called into the silence of the night.

Those weren’t his scarcely functioning blinds, but they were ones he knew well.

Castiel turned his head minutely to the left as if needing more confirmation, like the soft puffs of warm air that ghosted his bare shoulder and the soft snores weren’t enough for him.

His heart plummeted.

His face smoothed, youthful, free of worry lines and that little crease he gets above his nose when he concentrates. Perfect fan of dark eyelashes kissed is pale freckled skin hiding the beauty of mossy jade eyes behind them, the ones he knew glinted with gold when the sunlight caught them.

He looked like a vision while he slept. So tranquil, so peaceful, no idea that his night in a shared bed sent his best friend into a whirlpool of despair and regret.

He let it happen again.

Castiel had promised after the last time that it would be the last time, and yet somehow, they always found themselves falling into bed together (and if he’s being honest, there had been at least another three “last times” since that first time).

Like he could ever say no to Dean Winchester.

It wasn't because they had been best friends since high school, or the fact the sex was bad – the sex was some of the best Castiel had ever had in his entire life! but that’s where the problem lay. To Dean it was always just sex. Another nameless face in a bar, another wild night, another morning with zero attachments and when he came out as bisexual a year ago, well that just made everything a whole lot worse, didn’t it?

Before, when he was picking up women, Castiel had some semblance of peace with that; he hated it, but it was manageable. But now Dean was picking up every Tom, Dick and Harry alongside the Suzie’s, Michelle’s and Laura’s. Even though they're 8 years out of high school, both in good careers and seen by society as “adults”, he still felt like that lonely 18-year-old boy who watched the man he adored go to prom with Lisa Braden instead of him.

That was the night he realised he was in love with his best friend. A feeling he hoped would diminish over the years, but it was never the case.

Sure, there had been plenty of lovers & boyfriends in Castiel's life, but none of them matched Dean. A man whom he thought would never be interested in him, and yet, here he was, lying in his bed as naked as the day he was born, while the object of his affections slept blissfully beside him with an arm draped over Castiel’s stomach.

The first time it happened it had been a clumsy affair (Castiel fell out of his bed in excitement, which sent Dean laughing hysterically), but it didn’t diminish the mood. Every time they kissed Dean would bless him with a shy smile that was all teeth, the flush across his pale skin made those freckles stand out even more, that mossy-jade stare lit up every time Castiel moaned his name. He still gets goosebumps as he remembers so vividly that whisky-soaked warm air ghosting over his ear as he purred, “you gonna come for me, sweetheart?”.

By God, it was the best night of Castile's life.

He stupidly thought it was the start of something between them, even if Dean had gone long before he had awoken with nothing more than a text message saying he had to go to work and to not forget to lock up his apartment. But what cemented his falsehood was later that day when he caught sight of Dean with his arm around the shoulder of another woman, not even recognising Castiel's presence as he led her out of the bar. He had never been so devastated in his entire life. He was a fool to think it was nothing more than what it was.

Castiel had been angry, had refused to even acknowledge his existence and ghosted him for days. He would have probably been free of him if not for their mutual friend Charlie intervening. Worried by his silence he ended up spilling everything, twisting some of the truths so as not to give away his decade-long deepest darkest secret, and she had been nothing more than a solid comfort. But his anger turned to guilt the moment Dean turned up unannounced on his doorstep the very same day. Staring him down with wide, sorrowful, puppy dog eyes as he apologised profusely for what had happened. That if Cas was uncomfortable with it, they could just forget it ever happened. That Dean didn't want to lose him over something like this. It had Charlie's fingerprints all over it, or at the very least her encouragement, but it didn’t stop them from waking up together in Castiel's bed the following morning.

At least that time Castiel knew what this was, not that it made the ache in his chest any better.

He could feel his heart thundering against his ribs, the tears already stinging his eyes and blurring his vision. He needed to get out of here before Dean woke up and would question the state he was in; he’s not entirely sure if he could keep it a secret from him anymore.

Lifting Dean's arm gently so as not to disturb him, laying the limb carefully on the empty sheets and watching as Dean unconsciously pulled it closer to his body and he slid out of bed.

He dug around for his jeans, kicked something to the floor and retrieved the phone from the pocket. 20% battery left, not ideal, but enough to at least get himself an Uber. Dressed and with the car less than 5minuets away, he bid his sleeping best friend a silent farewell and slipped out quietly into the early morning light.

The driver was just as quiet as he was (which he was beyond grateful for), the radio was softly playing some country station that Castiel didn’t know existed, but it was the furthest thing on his mind – between his pounding headache and trying to keep himself held together long enough to not cry in front of a stranger. The journey was short and truthfully Castiel could have walked it, but he just wanted to get home, to the sanctity of his apartment. What he didn’t take into consideration was meeting his brother as soon as he walked through the door.

Gabriel sat at the kitchen table, eating her breakfast to start his day. Dressed in what he wore to bed (which wasn’t more than an overly large pair of boxer shorts with red hearts plastered all over them) his golden curls unruly and sticking out at all odd angles with day-old stubble ghosting his chin. How could he have forgotten that his baker brother started his workday at the crack ass of dawn?

Gabriel eyed him curiously; a spoonful of cornflakes raised to his lips as they curved into a flirty smirk. “Walk of shame?” he purred with question eyebrows wagging, “atta boy!”

Shame was right. The thought of it was like the final swing of the sledgehammer that brought his wall crumbling down. His eyes blurred as his chest tightened, and as soon as the first chin-quivering sniffle left his lips the spoon in Gabe’s hand dropped back into the bowl with a clatter and splash of milk. He reached his baby brother in a few strides, wrapping him up in his arms while Castiel sobbed.

 

…::::::…

And I cry, it's not fair
I just need a little lovin', I just need a little air

…::::::…

 

Castiel sat slumped at the kitchen table, a half-drunk cup of coffee cooling in front of him. He hadn't taken a sip since Gabriel poured it 10 minutes ago. The steam had long faded, just like the illusion that he could keep pretending everything with Dean was okay.

“I’m gonna kill him,” Gabriel announced, voice low and deadly serious, standing across from him, arms folded, eyes sharp and mouth twitching in frustration. He’d abandoned his breakfast the moment his little brother broke down in the doorway, sat soggy and forgotten in the bowl across from where Castiel sat. But at least he had to grace to pull on an old t-shirt embroiled with the words “Whisk Taker”  – but, no pants, still strutting around the place in those ridiculous boxers.

“No, you won’t,” Castiel said flatly, eyes fixed on the swirling patterns left in the coffee as it cooled

“Fine,” Gabriel huffed, pacing now. “But I can make him wish he never laid a hand on you.” Castiel huffed a soft, humourless laugh as his stare finally lifted to level his brother with a disparaging look. “Oh, come on, Cassie. Let me play the protective big brother card here!” Gabriel whined as his arms fell to his sides with a dejected flap.

“It wasn’t like that,” Castiel murmured. “Nothing that happened was… unconsensual.”

“And yet here you are,” Gabriel shot back, gesturing toward the crumpled tissues beside the mug, “snivelling at my kitchen table like someone kicked your puppy.”

Castiel winced but didn’t argue. He picked at the chipped crack in the handle of the plain white mug as he muttered, “I just… let it happen again. I keep letting it happen.”

“You can’t keep doing this to yourself, Cassie,” Gabe said, voice quiet now, more grounded. “For your own sanity, if nothing else.”

“I know,” Castiel whispered. The shame in his voice.

Silence hovered between them for a beat before Castiel said, so softly it was almost lost in the buzz of the fridge, “I just…” His lips pressed together, and his eyes burned again. “I love him, Gabe.” He laughed wetly, a choked little sound. “God, I sound so pathetic.”

Gabriel let out a slow breath, reaching over to squeeze his brother’s wrist. “You’re not pathetic. You’re just in love with a moron who doesn’t know how to express his feelings.” Castiel huffed a non-existent laugh as he finally lifted the coffee to his lips for a bitter sip.

“You know what you need?” Gabriel asked suddenly, pointing a finger dramatically toward him.

“A lobotomy?”

“Revenge,” Gabe smirked with a devious glint in his stare.

Castiel's brow knitted. “I… I don’t see how that’s any better.”

“No, think about it,” Gabriel said, suddenly animated, like the schemer in him had been just waiting for the right moment to take the wheel. “Charlie’s birthday thing is this weekend, right? It’s perfect.”

Castiel raised an eyebrow. “I still fail to see how my emotional collapse is party material.”

“Not for that,” Gabriel scoffed. “For this plan.”

“Plan?”

“Find a guy,” Gabe said, pacing again like he was outlining a military operation. “Someone hot. Someone charming. Latch onto his arm, make him feel special – hell, maybe he makes you feel special for once. Laugh at his jokes, toss your hair, wear those jeans that hug your hips – you know, the slutty ones—”

“Gabriel…”

“—Let one thing lead to another, and I can guarantee you won’t be thinking about farm boys from the Midwest clad in flannel for much longer.” He turned to his brother, beaming from ear to ear like he was some world great mastermind. “What's a better revenge than showing him that last night meant nothing to you, that he doesn’t matter to you?”

“But he does matter to me,” Castiel admitted quietly. His voice cracked around the edges. “I can’t pretend he doesn’t.”

Gabriel’s smile turned soft and a little sad as he moved to reclaim his seat opposite his brother, still considering him with a soft, caring look. “I know he does. But he doesn’t need to know that. Does he?”

Castiel looked away, blinking fast and trying to stem that telltale burn. The part of him that still ached for Dean's arms, his laugh, the way he always smelled like soap and leather and summer, that part wanted to cling to hope. But another part, the part that had spent the morning trying not to cry in the back of an Uber, knew Gabe had a point.

Revenge wasn’t the right word. It wasn’t even about being scorned and getting back at Dean, not really. He knew he was an addict who was hooked on finally getting the attention he so desperately craved from the man he adored. But just like any addiction, it slowly chipped away, decaying and destroying from the inside out.

It was about time he took some of himself back.

He can’t go on like this forever.

 

…::::::…

Think I'm gonna call it off
Even if you call it love
I just wanna love someone who calls me "baby"

…::::::…

 

The bar was already buzzing by the time Castiel and his brother arrived. Rainbows hung in every corner of the place – fitting for a gay bar – and music pulsed through the floor, a mix of retro dance and modern synth-pop, the kind Charlie loved. He spotted the birthday girl across the room, looking very elegant in what only he could describe as an elven red dress that fell just to her knee, glitter shimmered on her skin under the twirls multi coloured stage lights and a pair of pink Converse that both matched and clashed with her aesthetic. The little crown atop her copper-red hair declared that it was her birthday and matched the bright pink fairy wings on her back. The “magic” fairy wand in her hand – with a star on the tip and thin glittering streamers – swayed and fluttered as she used it gesture to the table of bystanders who were gathered around in a large circular booth that was decorated to the nines in banners and balloons, looking like she was holding court to her subjects like the queen she was.

Somebody at the table pointed towards their direction, Charlie turned, and her face lit up. “Novak’s!!” she screeched, running full sprint across the crowded bar and straight into Castiel’s arms first.

“Happy Birthday!” Castiel greeted her with a tight hug, chin over her shoulder and swaying her gently.

As he pulled back, he saw him.

Dean had been sitting hidden behind Charlie as she stood at the table, eyes locked onto his.  

Castiel’s stomach dropped.

He could do this. That man was no more than a stranger to him tonight.

He pulled his attention away just in time to see Charlie dive into a hug with his brother. Gabriel wrapped her in a bear hug and lifted her from the ground, which warranted him a childlike giggle. “I didn’t think you were coming!” she scolded when she was finally lowered to the ground and batting Gabriel on the chest with the star-end of her fairy wand.

“Just a drive by I’m afraid, someone's gotta open up the bakery in the morning. Just here to make sure Cassie arrived safely—” Castiel rolled his eyes and shook his head, but he was secretly grateful to have a shield, albeit temporary “—and to wish the Queen a very happy birthday.” He added, taking Charlie by the hand a pressing a kiss to her knuckles. She chuckled again, batting him playfully with her wand, but she was immediately distracted by someone behind them, more guests, Castiel assumed. She greeted them with hugs and pleasantries before turning back to the brothers and pointing towards their designated booth.

“There's a round of shots on the table. Help yourselves, I’ll be over in a sec!” she added hastily before being swept away by the new group of arrivals. Now was the moment of truth. Castiel led the charge with his brother tailing behind. His firm grip on his shoulder as if psyching him up for a prize fight as he murmured into his ear, “You got this, champ! Don’t back down. Take no prisoners.”

Dean’s eyes watched his every step as he advanced on the table, but didn’t make a move from where he remained seated. There were a few familiar faces that Castiel recognised, mutual friends of Charlie and Dean’s that he had met once or twice and greeted them all with pleasantries and familiarity.

A large tray of glittering shots sat in the centre of the table, a kaleidoscope of colours that shimmered under the dim bar lights – like someone had melted an alcoholic pride flag into a dozen plastic cups. Gabriel reached for two without hesitation. He handed the brightest orange one to Castiel, keeping a bubble-gum pink concoction for himself. “Liquid courage,” he smirked as he clinked the rims of the plastic mini glasses and knocked his back. Castiel followed suit. The orange hit his tongue with the sharp tang of artificial citrus and a burn that raced down his throat like fire. He grimaced and blinked through the aftertaste.

And then... “Hey, stranger.”

Castiel turned slowly, eyes locking with Dean’s. He looked good, like he just walked straight off the cover of a GQ magazine. Hair perfectly styled into that short, spiked look he so often wore, denim button-down open, that golden amulet pendant his brother bought him for his 18th birthday sitting over the top of a plain black t-shirt. His freckled cheeks hidden behind a layer of silver and pink glitter – Charlie's doing no doubt – and a small, tentative, unsure smile twitched at his lips. One hand wrapped around a beer bottle, the other deep into his back pocket, looking almost awkward, uncomfortable, his shoulders tense like he was bracing for a hit.

“Hello, Dean,” Castiel replied, his tone cool and flat. Not hostile, just distant.

Dean's eyes flicked to the tray of shots like he needed something else to focus on. “The-uh… the green ones are pretty good,” he offered with a light chuckle. But when Castiel didn’t reach for one or even seemingly acknowledge his words, he added, “What, uh… what’ve you been up to? I-I haven’t heard from you in a hot minute.”

“Been busy,” Castiel replied shortly. No explanation. No warmth. Eyes trying to look anywhere but at that face, that flawlessly stunning freckled – and now glittery – face.

Dean shifted his weight from one foot to the other. “Yeah. Right. Of course.” He opened his mouth again, hesitated. Cleared his throat. “Listen, Cas, I gotta—”

Gabriel slapped a casual arm over his brother's shoulder, “I don’t know about you, bucko, but I could do with a drink that isn’t covered in edible glitter.” Castiel was startled by the gesture but didn’t resist as Gabriel turned him gently by the shoulders and began steering him toward the bar, giving Dean a pointed smile that didn’t quite reach his eyes as he threw an “Excuse us” over his shoulder as he led him away.

Once they were a few steps away, Castiel let out a breath he hadn’t realised he was holding. “Thank you,” he murmured

“No problem,” Gabriel said, dropping his voice as they walked. “Just doing my sacred big brother-slash-wingman duties.”

Castiel didn’t respond. But as he glanced over his shoulder – just once – his eyes found Dean still standing there, hand still in his pocket, shoulders still hunched, looking a little lost.

And for a second… just a second… Castiel’s cold resolve wavered.

 

…::::::…

You can kiss a hundred boys in bars
Shoot another shot, try to stop the feeling

…::::::…

 

The night slipped by in a haze of neon lights, pulsing music, far too much glitter and the low hum of alcohol in Castiel’s veins. He’d started the evening stiff and guarded, but something about the way Charlie had flung an arm around him and demanded he play “Never Have I Ever: Regret Edition” cracked the wall just enough to let the warmth in.

Castiel found himself laughing – real, gut-busting laughter – surrounded by Charlie and her friends, who were a chaotic, glitter-smeared blur of mischief and terrible ideas and glow sticks. To his own surprise, Castiel even danced.

It wasn’t graceful. His hips moved with the fluidity of a disgruntled scarecrow, his shoulders too stiff and self-conscious. But it didn’t matter. Charlie screamed in delight while Gabriel almost died from laughing.

But even amid the laughter, he could feel his stare.

Every time Castiel swayed to the music or laughed a little too freely, he felt eyes burning across the room. And every time he looked, he caught glimpses of Dean — leaning against a wall, barely nursing a drink, a ghost of his usual charisma. He wasn’t mingling. He wasn’t smiling. He looked… dare Castiel say it? Sullen.

Good, Castiel thought, lips twitching around the rim of his drink.

Call him petty. Call him a little tipsy. But watching Dean frown across the room like a kicked puppy gave him the tiniest, wickedest flicker of satisfaction. Let him stew in it.

Even Gabriel, who swore he’d “only stay for an hour tops,” had somehow become the unofficial party mascot. Commandeering a pair of comically large heart-shaped sunglasses, a rainbow clown wig, and Charlie’s fairy wand, and occasionally poking Castiel in the ribs with it for emphasis.

He waved Charlie’s wand with flourish, twirling it through his fingers like a carnival magician as he stumbled over to Castiel from the dancefloor, sunglasses sliding down his nose as he slumped into the booth beside his brother, sweat and glitter clinging to his forehead.

“Shouldn’t you be heading home?” Castiel asked over the music, leaning in so Gabriel could hear him.

“What? And miss all the fun?” his brother shot back, eyes wide with mock offence. “Are you trying to get rid of me?”

“You have a bakery to open in…” Castiel checked his watch with exaggerated drama. “6 hours!”

Gabe waved his wrist dismissively with an “Eh.” As he sank further into the seat. Then, without warning, he bopped Castiel on the nose with the wand. “I command you to get me another drink!”

Castiel frowned, snatching at the wand mid-swish and missing. “You know that’s not a real wand, right?” But Gabriel just did it again. And again. The boops got faster, more chaotic, until Castiel finally swatted his hand away. “Alright, alright!” With one final flick of the wand Castiel caught it, stealing it from his brother's hand and using it like a conductor’s baton to point at Gabriel dramatically. “I’ll get you another drink. Just stop hitting me!” he said, smacking the centre of his brother's glittery forehead for emphasis.

A chuckle stopped him. It was quiet. Almost buried under the thrum of the bass and the cackle of Charlie’s latest dare. But Castiel heard it. Felt it.

Dean.

At some point, he had slid into the booth opposite them, bottle in hand, smirking around the lip of it like he’d been there the whole time. His eyes glinted with something between amusement and nostalgia, like he was watching an old home movie.

For a brief moment, Castiel froze. Their eyes locked.

Then he looked away as he shoved his brother out of the booth so he could actually get out the booth. He didn’t say a word. Just turned on his heel and headed for the bar, heart thudding too loudly in his ears. Handing Charlie back her wand on the way and giving her strict instructions not to let his brother get hold of it again.

The line at the bar wasn’t long, but it moved slowly. Castiel leaned against the counter, letting the music wash over him while he tried to shake off the heat lingering in his chest. He hadn’t expected Dean to affect him this much if he did.

He was not going to give in.

“Long line just for glittery drinks,” a warm voice said beside him.

Castiel turned and found himself face to face with a man he recognised from the party group – sharp cheekbones, a clean suit jacket despite the chaos around them, and a crooked smile hidden behind a dark 5 o’clock shadow and an accent that enthralled Castiel. British, if he wasn’t mistaken, not that prim proper accent Hollywood bad guys always depict, but relaxed. Polished around the edges, but approachable.

Mick Davis. One of Charlie’s co-workers, if memory served.

Castiel offered a polite nod. “Tell me about it.”

Mick leaned on the bar beside him, eyes scanning the drink menu with mild disapproval. “Half these cocktails sound like hangovers in a glass. Though the ‘Unicorn Heart Attack’ does have a certain… ominous appeal.”

Castiel huffed a quiet laugh. “That one tastes like birthday cake and regret.”

“Oh, so you’ve tried it.” Mick smiled, then glanced at him more directly. “Let me buy you something a little less dangerous.”

Castiel hesitated. Then smiled back, a small, slow curve of his lips. “Sure.”

This had been Gabriel's plan after all, right? Find a nice guy to treat him well and to forget about the stare he could feel burning into his back like a curse he couldn’t shake.

Let him watch.

Eventually, Gabriel made his grand exit – complete with an exaggerated bow – much to everyone’s disappointment. But for once, Castiel didn’t feel like he needed his brother around as a human shield against Dean. Not when he had Mick.

Mick was easy company. Effortlessly charming, all crisp vowels and soft British sarcasm. A true gentleman, but still quick to roll with Charlie’s chaos and even Gabriel’s nonsense before he left. He fit in surprisingly well with the group, slipping into conversations with ease, drawing out laughter like he belonged.

Well… almost everyone seemed to warm to him.

Dean hadn’t said a word, but Castiel could feel the tension every time he turned his head. The weight of Dean’s stare was unmistakable – sharp, guarded, watching Mick like he was some kind of threat. His jaw was tight, the muscle ticking as he chewed the inside of his cheek, eyes narrowing just a fraction more every time

And Castiel… let him watch.

Dean’s glare hadn’t wavered in the last ten minutes. He wasn’t drinking anymore. Just sat hunched in the booth like a thundercloud, chin resting in his palm, his other hand drumming an anxious, angry rhythm against the table. His eyes were locked on Castiel like they had teeth, like he was a moment away from doing something reckless.

Castiel pretended not to notice – but he did. Of course he did. Could feel Dean’s gaze burning a hole between his shoulder blades, heavy and possessive, the weight of it coiling in his spine like a warning. His jaw tightened.

What the hell did Dean think he was doing?

Cas laughed again at something Mick said, but it was forced now. Hollow. He could feel himself fracturing under the scrutiny. But he continued to hold his own, because if he did, he might march over there and say what he was thinking.

“You don’t get to look at me like that. You don’t get to act jealous when you don’t want me. You don’t get to guard something you never—”

“You alright?” Mick asked, leaning in slightly, voice soft over the music.

Castiel blinked. “What? Oh–yes. Sorry, just thinking.”

Mick offered a warm smile, the kind that suggested charm without cost. “Want another drink? I’m buying,” he offered, already flagging down the bartender like it was a done deal. But before Castiel could answer, Mick pivoted, voice dipping low as he leaned in close, breath brushing hot against the shell of Castiel’s ear.

“Or… maybe you want to get out of here?”

The hand Mick placed at the small of his back was subtle, but too familiar. Too presumptive. Castiel stiffened.

His touch wasn’t aggressive, but it wasn’t welcome either. It wasn’t dangerous and just all kinds of wrong. Off in a way that made his skin crawl, a quiet tug in his chest that whispered this isn’t it. He stepped back half a pace, enough to break the contact without causing a scene, but the discomfort lingered as a cold ripple under his skin.

And before Castiel could answer, Dean’s voice cut through the music like a knife. Cold, clipped and on the verge of furious. “Cas. Can I talk to you?”