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Two years ago, Sam and Jess made the decision to break up. Though they had planned on going to Stanford together, Sam reluctantly decided to stay in Lawrence after graduation at his father’s behest, and after a year of trying to make it work, they decided that neither wanted to put the other under the pressure of a long distance relationship fresh into their college years. So they decided that parting on good terms would be better than the slow suffering.

The moment that Sam said goodbye to Jess, he began to regret all of his decisions. He felt as though his life no longer had direction. The images he’d had of a happy future all hinged on graduating from Stanford Law, marrying Jess, and starting a family. Instead, Sam spent the last three years studying part time at the local community college while helping out on his free days with the family business, restoring classic cars at John & Bobby’s garage.

He had also taken to casually dating girls that were as different from Jess as he could find and he outright refused to talk about Stanford.

 “Come on, Dean. Please?” Sam pleaded.

“Dude, I am NOT going on some blind date just so you can hook up with Ruby,” Dean answered with distaste. Sam’s latest fling was definitely Dean’s least favorite so far. Sam rolled his eyes in exasperation.

“It’s not a date, Dean; it’s a group thing. And yeah, Ruby’s bringing her sister, but Jo’s working tonight and Charlie said she’ll be there too, and I told her I’d bring you. And if I don’t--” Sam frowned at the thought. “She’s like… a really angry kitten. With sharp claws.” He curled his fingers like a cat for emphasis.

Sam knew that Dean wouldn’t have plans, even though it was Friday night. Unlike himself, Dean hadn’t had much of a social life since he and Lisa broke up last year. The split was amicable and the two remained friends, but something seemed different about Dean lately. In fact, he and Sam had somehow changed roles, with Sam now being the Winchester more likely to bring home a random waitress than his once infamously womanizing older brother.

He gave Dean his best sad puppy eyes, knowing that his brother really had no excuse to turn down the offer anyway.

“Fine,” Dean relented, “but you’re paying the tab.”

“Deal,” Sam breathed in relief.

***

Sam slammed the heavy passenger door of Dean’s ’67 Impala as soon as they were parked in the lot beside The Roadhouse. He stomped off toward the door, clearly relieved to have finally escaped the confines of the vehicle.

“Hey! Manners!” Dean yelled after him with false indignation, failing to hide a smirk as he stroked his hand over the car’s roof soothingly. “He didn’t mean it, Baby.”

Dean might have used the 20-minute drive to the bar to amuse himself by mercilessly annoying his younger brother. He’d managed to cover an impressive array of topics in the short time, concluding with Sam’s steadily lowering standards when it came to dating.

“Jerk!” Sam yelled back before swinging open the green wooden door and disappearing inside.

“Bitch!” Dean shouted back, followed by a smug grin.

A neatly dressed man sitting alone on a bench beside the entrance chuckled at the exchange. Pleased with the fact that even a perfect stranger could see the amusement in his brother’s annoyance, Dean called over to the man as he closed his own door and headed toward the entrance, “No respect for a classic!”

“Kids these days,” the man responded with a solemn shake of his head, and a flash of a smile just as Dean threw his head back in laughter and passed through the door to enter the bar, his mood lightened.

Inside, he waved a greeting to Jo Harvelle, the pretty blonde behind the bar, before making his way to one of the booths that lined the wall. Sam, still pouting a bit, sat facing away from the door with the wall on his left side with Ruby at his right, so Dean slid onto the bench opposite. His pleasant mood was enough that he even greeted Ruby with a polite smile as he settled into his seat.

“So, uh, where’s the rest of this group thing?” Dean asked, just as Jo reached the end of their table with a bucket of ice that held six beers.

“Charlie said she’s running late,” Jo commented offhandedly. Sam and Dean both eyed her with suspicion as her cheeks and ears turned pink.

“Well, hi there, Jo,” Dean greeted with exaggerated cheerfulness. “Something you wanna share with the class?”

 “Nope,” Jo answered, quickly turning on her heel and ducking back behind the bar before she could be asked any further questions.

The Winchesters thought of Jo like family, along with her mother, owner of The Roadhouse, Ellen. Dean couldn’t remember exactly when Ellen had first appeared at their Uncle Bobby’s side, but he’d been a young teen. It seemed like she was an instant fit and she’d been around ever since. She and Jo were two of a kind, sweet but tough, and afraid of nothing.

Charlie had been patiently pursuing Jo for weeks now, but as far as they knew, her attempts had so far been unsuccessful and the pair’s interactions had gone no further than friendly chatting at the bar.

“I think Charlie’s persistence is finally paying off,” Sam laughed, picking up his bottle and taking a draw, the annoyance from earlier finally melting from his face.

“Meg’s on her way. Her date’s meeting her here,” Ruby stated without looking up from the text she was reading. Her face twisted with disapproval as she scrolled on. “Castiel,” she read. “Stupid name.”

“I like it,” Dean challenged with a glare, his tolerance for Ruby dipping dangerously low, “It’s different.  Better than some douchebag name like Brady.” Sam huffed a laugh; Brady had been Sam's best friend until he tried hooking up with Jess behind his back and Dean had nearly beaten him to a pulp when he found out. Ruby glanced up, but said nothing. “Date, though? I thought this was just a casual group thing,” he added, recounting Sam’s words from earlier in the day.

Ruby looked up from her phone, one eyebrow quirked upward. “What do you care? You interested? I could probably still make it happen, you know.” She held up her phone up to imply that she could easily arrange such a tryst between he and Meg with a simple text.

“What? Hell, no! I just meant--” Dean stammered. He hadn’t even met this Meg girl yet, but he already knew that he was not even remotely interested.

“Dude, chill. I’m just messing with you.” Ruby laughed, though Dean suspected that hadn’t been joking at all about making that arrangement if he were really interested. “I didn’t know she was bringing a date,” she shrugged, “but that’s Meg. She likes ‘em rich and pretty. Unless they’re really rich. Then pretty is negotiable.”

Dean frowned, deciding that he was going to like this Meg even less than Ruby. Sam had carefully averted his eyes, avoiding the glare that Dean was now burning into his forehead for dragging him out tonight. Dean briefly considered bailing to the parking lot, but decided that once Charlie arrived, he’d be able to ignore Ruby for the rest of the night if he had to.

After a few more minutes of painful small talk, the infamous Meg finally walked through the door. Much like her sister, she was small and dark haired, with a sullen look about her. Just behind Meg stood the man that Dean had shared a laugh with in the parking lot. He had apparently been waiting in the late November chill for Meg this whole time and that already made Dean like her even less.

Dean didn’t know if the guy was rich, but now that he could see him properly, he thought he definitely fell into the pretty category. Castiel was close to Dean’s height, tanned with dark messy hair and hypnotic blue eyes. He had just the right amount of stubble and was currently pulling off a slim-fitting leather jacket, revealing broad shoulders under a white button-down shirt. It wasn’t until Dean’s eyes had tracked from the man’s lips to where he was rolling up his sleeves to bare strong forearms and then to his well-fitted jeans that he realized he was practically ogling the guy. He turned back to focus on his beer, hoping that no one had noticed.

As Meg and Castiel approached the table, Ruby slid out of her seat to greet them, tugging her sister away by the wrist and off toward the bar, leaving Castiel standing awkwardly abandoned at the end of the table.

“Kids these days, right?” Dean commented with an amused smile, resulting in a laugh from Castiel. Dean held up one of the full beers and sat it down on his side of the table, inviting the man to sit.

Sam looked between his brother and the newcomer with slight confusion before asking, “Have you two met?”

The man gave a noncommittal shrug as he slid into the seat beside Dean, smiling briefly at both, “Not officially.”

“Dean Winchester," Dean offered, shaking Castiel’s hand in greeting, “and this sasquatch here is my little brother, Sammy.” The man’s hands were strong, but gentle, and Dean felt silly for thinking such a thing.

“Just Sam, actually,” Sam added, shaking Castiel’s hand in turn. “You must be Castiel.”

“Castiel Novak,” he confirmed. “It’s nice to meet you both.” His voice was deep and his eyes were such an electric blue that Dean could barely tear his own green eyes away.

And damn it, if Dean didn’t have a crush on this guy already.

He shook away the thought, going over all the reasons that made the idea ridiculous. First of all, they’d only just met, and Dean was not some kind of Disney princess falling for the guy at first sight. Secondly, this man was here on a date with Meg, and Dean had no reason to assume that he was even attracted to men. And, most importantly, Dean had absolutely zero experience with dating men anyway. He’d finally come to terms about his own interest in men after realizing the attraction about 3 years ago, but he had never actually acted upon it, nor had he mentioned his revelation to anyone else.

The first time he’d realized that he felt attracted to a man, he had panicked, diving headlong into his first and only long-term relationship with the first woman he met. Things were going well with Lisa and her young son Ben at first but the chemistry just wasn’t there, and after almost 2 years, Lisa finally called it quits.

“So, Cas,” Dean began, “First date?” The three men glanced toward the bar to see Jo pouring Meg and Ruby each a shot of some dark liquid.

Castiel looked apprehensive, hesitating a moment before answering. “I guess you could say that. Actually, I wasn’t given much choice in the matter. Meg works on another floor of the hospital where I work. She cornered me in the cafeteria and told me to meet her here at 8 o’clock because we had a date. I agreed before I even knew what was going on.” He ran his hands through his hair sheepishly, effectively making it stand up even more than it already did. The bedhead look suited him, Dean thought.

“Wow,” Sam remarked with a small laugh. Dean threw an annoyed glance at Meg who was now flirting with a stout man in an expensive suit.

“Yep.” Castiel nodded, “Now I just have to figure out how to tell her I’m gay.”

It took a moment for Castiel’s statement to wash over Dean, and when it finally did, it hit him like a tidal wave.

Okay, so Cas likes dudes. So what? That doesn’t mean anything. It doesn’t mean he likes me. It doesn’t mean I’d try. It doesn’t mean anything, Dean thought frantically. Besides, he’s still on a date with Meg. But is it really a date if Meg just kinda bullied him into showing up, then made him wait out in the cold and ignored him? Bitch…

The possibilities, some realistic, most insane, flew through his mind dizzyingly fast. Dean was pulled from his momentary internal panic by the sound of a familiar voice.

***

“What’s up, bitches?!” The cheery redhead grinned as she flung herself into the booth beside Sam, who instantly wrapped a long arm around her in greeting.

“Hey, Charlie,” the brothers chorused with surprise, beaming with genuine smiles for their friend.

Charlie and Dean had developed an odd but meaningful friendship during high school. They met in detention where both were frequent visitors, and gradually the two became friends.Dean had placed his trust in her, opening up about his life at home with his father, who’d gone a bit off the rails after his mother’s death. Charlie had promised to always be there for him and had lived up to that promise. In the last few months, she’d even managed to rope Dean into playing the role of handmaiden to the queen of Moondoor, who happened to be Charlie herself, in monthly LARPing events.

She and Sam had also developed a close friendship, bonding over their mutual love of tech gadgets, gossip, and college courses they’d shared. She, like Dean, wanted the best for Sam and had gotten closer than anyone to discussing Jess and Stanford with him.

“So, who’re we telling we’re gay?” she asked, having overheard the boys talking while she walked up. She thought Dean would have seen her approach, but he’d seemed oddly lost in his own head.

“That would be my ‘date’,” the handsome stranger answered, using air quotes.

“Charlie, this is Castiel. He’s here with Ruby’s sister Meg tonight,” Sam gestured toward the bar where two women were giggling flirtatiously with the man Meg had been talking to earlier. The man seemed to be paying for another round of shots they were sharing, sliding a few bills to Jo as she poured.

“Nice to meet you, Castiel. And samesies!” She flashed a toothy smile. “The gay thing, I mean. See that gorgeous girl behind the bar? She wants me.”

Dean ducked his head in laughter, coming out of whatever fog he’d been in. “Does she know that she wants you yet?”

“Quiet, handmaiden,” Charlie quipped in return.

“Handmaiden?” Castiel asked with a teasing smirk, turning to lock eyes with Dean whose ears had quickly turned a brilliant shade of red.

If she hadn’t know better, she’d think the two men seated across from her might have been on their first date. Dean looked shy and nervous, rubbing a hand on the back of his neck, stammering through his lame explanation while Castiel smiled at him with amusement. She looked up to Sam, but he seemed oblivious to what she was seeing. Or at least, what she thought she was seeing, which was subtle but definite flirting.

Meg and Ruby approached the table, each carrying a fruity cocktail. Instead of sitting, Ruby stood at the end of the bench, frowning at the sight of Sam with his arm still draped over Charlie’s shoulders. Charlie noted Ruby’s contempt but was too entranced in Dean and Castiel at the moment to address it. Instead she allowed Ruby to reclaim her position at Sam’s side while she pulled up a chair at the end of the table. Meg, however, had pushed herself onto the opposite bench, crowding Castiel into Dean while she pressed against his side.

For the three to fit, Dean raised and rested his arm on the back of the bench behind Castiel’s shoulders, careful not to touch him. Meg had placed herself practically in Castiel’s lap, ignoring the look of discomfort that instantly crossed his face. Charlie watched on in curious amusement.

“I don’t think we’ve been introduced,” Charlie said, directing her attention toward Meg. “Charlie Bradbury. Long-time friend of these handsome fellas,” she made finger guns at the brothers.

“Meg Masters,” she drawled, uninterested.

Charlie bit her cheek and pulled a beer from the ice bucket. “I’ve already met Castiel here. How did you two meet?” she asked, wiggling her fingers at Meg and Castiel. Meg perked up, clearly keen to flaunt her attachment to her handsome date.

“Clarence here is an angel,” she said, running a finger across his chest. “He’s a pediatrician at the hospital where I work.”

Castiel cleared his throat and shook his head, directing his words to Charlie. “I’m a pediatric physical therapist,” he corrected. Meg pouted with disappointment.

“That’s awesome, Clarence,” Dean chimed in, and now it was Castiel’s turn to flush. “Really, though, helping kids, man? That’s great.” Charlie couldn’t hide her grin.

“Yeah, what’s that like?” Sam asked. “I mean, working with kids?”

Meg groaned, cutting Castiel off. “Ugh, I really don’t know how he does it, kids running around and having to entertain them like some kind of clown all day. And all of the noise all the time. No thank you. I’ll stick with the old bedridden geezers upstairs.”

“Old people are assholes too,” Ruby added. “Luckily for me, working in luxury retail means no brats, but sometimes we get the old ones bitching about the prices.”

Charlie could see the danger in Dean’s face, and cut him off before he could respond to either of them. “Well, I get to work in a dark room with loud music and no one but my computer to keep me company. Heaven,” she sighed happily.

Castiel chuckled. “Actually, I love working with the kids. Their resilience in the face of adversity is inspiring. Plus I get to wear scrubs with honeybees and ducks on them.” The table broke into laughter, breaking the tension once again.

After a while of chatting, Charlie decided that she officially approved of Castiel, and seeing the fondness growing on Dean’s face, she supposed he was mere steps away from falling off a new cliff in his life. He’d never mentioned being interested in men before, but she had suspected for a while now.

About three years ago, just before Dean and Lisa started dating, the Roadhouse had hired a new chef—a sweet, burly man with a Cajun accent. When Jo introduced Benny to Sam, Dean, and Charlie, Dean had reacted with instant animosity. Charlie hadn’t understood Dean’s dislike at the time; Benny had been more than friendly. But Charlie saw Dean behave with Benny just as she was seeing him behaving now with Castiel—shy, nervous, and flustered. She suspected his attitude might have stemmed from attraction, but a week later Dean and Lisa were dating and Dean’s negative attitude toward Benny dissipated.

Charlie attempted to gently approach the subject with Dean, but he was quick to evade the conversation. And though she had been proudly open as a lesbian since her teens, she still knew better than to push a person before they were ready. It had not come as a surprise, however, that Dean and Lisa’s relationship struggled.

Now that the crowd had thinned, she excused herself from the table, and perched on a barstool near the center of the bar. Jo smiled as she made her way over.

“Hey, barkeep,” Charlie winked. “How’s it going?”

“I should be asking you that,” Jo replied, nodding toward the group at the booth. “What are you guys doing hanging out with those bitches?”

Charlie rolled her eyes. “Sam,” she said, as though this were explanation enough, but Jo seemed to understand.

“Ruby’s just a snob, but that Meg girl’s a real piece of work. She was over here making plans for a date tomorrow with some other guy.” She looked over at the Castiel. “What’s his story?”

Charlie looked over her shoulder. Dean, Castiel, and Meg were still crowded into one side of the booth, but the stiffness had waned while they talked and drank. Dean and Castiel looked more comfortable now, still seated hip to hip, each stealing glances now and then while the other wasn’t looking.

“He’s pretty great, actually. Physical therapist, works with kids, nice guy, funny,” she listed. “Gay.”

Jo nearly choked on the beer she was sipping. “Gay? Does Meg know?”

“Nope.” Both looked at the group again, just in time to see Dean laughing at something Castiel had just said and Castiel beaming at Dean’s response.

“Wait a minute… Red, am I missing something important here?”

“I have a theory.” Charlie smirked. “Have dinner with me tomorrow. We can discuss it over sushi.”

Jo squinted, giving Charlie a pointed look. “Make it Italian and you’ve got a date.”

***

Castiel hadn’t really known what to expect from tonight after being cornered into this “date” by the pushy hospice nurse. He certainly had not expected to spend the last few hours having great conversation with a fun group of people, give or take a certain few, for what he truly hoped would be the first time of many more to come. Sam was smart and witty, although Castiel suspected he may be hiding some pain. Charlie was funny and charming with her bold personality. And Dean… Well, he certainly had not expected Dean. While the man seemed to be cocky and confident on the exterior, there was definitely much more beneath, and Castiel wanted to learn so much more.

He hadn’t intended for it to happen, but he felt a sort of bond with Dean even before they’d been properly introduced. Of course, there was no point in pining over a straight man, although being crowded against one another all evening had been an unanticipated turn of events. Dean had turned stiff and tense against his side at first, uncomfortable with the unwanted touch, Castiel assumed. But as the evening went on he felt Dean relax, and though he wasn’t sure if he’d just imagined it, (wishful thinking, perhaps), it seemed Dean had even begun to lean into him, their legs pressed together from hip to knee, feet resting against one another, and Dean’s arm just behind his shoulder occasionally grazing across his upper back. Castiel felt sparks of electricity with each tiny touch.

Unfortunately, he’d also spent a large portion of the evening avoiding unwanted advances from his other side. Meg’s hand kept finding its way onto Castiel's thigh and she’d wiggled her way under his arm. As the night went on he knew that he needed to confess his disinterest before this went any further, however he was not looking forward to that conversation. He had a feeling that Meg wasn’t the type that faced rejection very often or very well.

“Y’know, I think Charlie just might be getting somewhere with Jo,” Dean said to Sam as they looked toward the pair at the bar.

Meg craned her neck to whisper into Castiel’s ear. “We’ll be getting somewhere ourselves as soon as we ditch this dump,” she hissed, pecking a kiss on his neck and gripping his thigh once again. He straightened up quickly, pushing her hand away. He had to put a stop to this now.

“I, uh, think we might need to talk… privately,” he could feel his face flush, and he glanced around the table quickly. Sam looked on with empathy while Ruby rolled her eyes, probably assuming that he would be propositioning her sister momentarily. Dean's face was difficult to discern, but there was a fleeting glimpse of a smile hidden under that forced neutral gaze.

***

Dean watched with bated breath as Castiel and Meg slipped their coats on and stepped outside to talk. He wondered how the conversation would go. Would he ease into it and let her down easy? Would he bluntly say it? He’s attracted to men. Dean wondered how he would say it himself, how the words would sound in his own voice. He’d never actually said them out loud before.

They didn’t have to wait very long to find out what Meg’s reaction would be. She stomped back into the bar with a scowl on her face. “Come on, Ruby, we’re leaving.”

Ruby separated herself from Sam without hesitation and pulled on her own coat. Sam looked annoyed, but not hurt, Dean noticed. As the sisters headed back to the door, Castiel stepped back inside facing their glares as they passed him without speaking. Once they were gone, he slumped back into the booth beside Dean.

“Sorry, Sam,” he said. When Sam looked confused, he added, “for my date ruining yours.”

“Oh!” Sam shook his head. “It’s fine. Going out with Ruby was probably a mistake anyway.”

“Trust me, you’re both better off,” Dean commented matter-of-factly. “Hey, Jo! Can we get another round?”

The mood was considerably lighter for the rest of the night. Charlie and Jo joined them shortly after when Jo’s shift ended. Dean and Castiel sat side by side with occasional bumps of their elbows or knees. They mused about bad dates they’d been on in the past, and filled Castiel in on their favorite funny stories about their little circle of friends, and Dean called for a toast when Jo finally admitted that she and Charlie would be going on a date tomorrow evening.

“About time,” Dean said with a smirk.

Charlie mocked a whisper across the table to Dean loud enough for the group to hear, “Don’t worry, I’ll give you all the details.”

“Like hell, you will,” Jo said, poking at Charlie playfully.

Dean’s chest swelled seeing the two interact. He loved them both, and if they could be brave enough to take a new step in their relationship, maybe Dean could be brave enough to take new strides as well.

He turned his eyes to Castiel, catching those intoxicating blue eyes once again. “Hey, Cas… can I, uh, get your number?” He nervously fiddled with his phone, setting it flat on the table and sliding it toward him. ”Y'know, for next time. We, uh—we should hang out again.”

Castiel smiled and accepted Dean’s phone, tapping at the screen. A moment later, he pulled his own phone from his pocket as it chirped a notification. “I’ve got yours now, too.” He held up his phone to show Dean the little yellow smiling face he’d sent himself.

Dean chuckled, pocketing his phone again with pink cheeks and a hard-to-hide smile. “Thanks.”

“No, thank you. Thank you all for taking me in tonight, especially after I ruined your date, Sam,” he replied.

Sam waved him off. “Dude, no worries. It wouldn’t have worked out anyway. Besides, we traded in two bad dates for a new friend. I think that’s a pretty good deal.”

Charlie had apparently been holding back some excitement for a few minutes now, because she pounced from her chair as though it were spring-loaded and hugged Castiel.

When they finally left the bar, Charlie tugged Dean off to the side as everyone said their goodbyes in the parking lot. “We need to get together for lunch, Winchester,” she demanded.

Dean raised his brow at her tone. “Um… sure? How about Sunday so I can get all the details about—” he lifted his chin toward Jo and winked.

Charlie relaxed and poked him in the center of his chest, “My place. Noon. Sunday. We’ll talk.”

“Will do,” Dean answered, hugging his friend.

As they returned to the others, Dean hugged Jo goodnight and Charlie swept Sam into a quick conversation about a class that he was currently taking. Dean stepped away toward Castiel, rubbing his hand over the back of his neck.

“So, uh,” he began, speaking toward Castiel’s shoes, “you—you have my number. Feel free to—you know—or whatever.”

Castiel didn’t immediately answer, but when Dean finally looked up, he hadn’t been expecting the wide, soft smile and those eyes waiting for him. He felt breathless and dizzy. It took him a moment to realize that Castiel had his phone in his hand and Dean’s own phone was vibrating in his pocket. As he retrieved his phone, Castiel zipped up his leather jacket and climbed onto a sleek gray motorcycle, pulling on a matching helmet. Dean’s eyes followed him as he started the engine, waved a goodbye, and pulled off into the night.

Dean watched until the motorcycle disappeared around a corner, before coming back to his senses. He smiled as he finally unlocked his phone and checked his message.

Cas (12:14am): Goodnight, Dean. Talk to you soon.