February. Dean ruffled his jacket up to his ears and hunched his shoulders as the cold wind yanked at his body and tried to weasel its way through him. He was walking up the front steps to his college campus building; he'd only been out of his car for a few minutes and still Jack Frost nipped at his nose. Goddamn February, so cold and grey and miserable. It was one of those months that just made people want to jump off a bridge and hit the solid ice below. Not just because it was one of the dreariest months of the year but also because of the 'holiday' that landed in the middle of it.

February wasn't really a warm time of the year, as much as people liked to pretend that it was the cold nights that made the warmest memories they were full of shit and they knew it. Valentine's Day; the day for lovers. That warm fuzzy feeling when you pass around over-priced cardboard and terrible tasting chocolate, but mostly when you receive it. Another commercial holiday to show people how popular they, how cared for.

At least that's how high school had been, college was different. Somewhat. People were older, yes, but that didn't make them smarter or change their choices. And really they weren't even that much older, just out of high school most of them and it was just another year of school. So for those college students with the cash to buy a locker for the year or semester, and the ones that were also socialites and gorgeous, receiving a valentine in the locker was possible.

And Dean did, he'd opened the creaky metal container to watch a bunch of little folded notes and cards flutter down to his feet, as well as a few wrapped gifts like chocolate and candies. A small smile crept to his lips as he heard some giggles down the hall. It was forced; he always gave that smile just in case the person who had hidden the notes was watching him. It was habit already; he wasn't even sure where it was coming from anymore. Dean stooped to pick the cards up and put them in a neat little pile as he prepared for his class. He'd always received these little cards and letters in high school, stuffed in his locker, his desk, hidden in his back pack or somewhere else that he'd stumble across it later.

Dean took the pile and as much as he wanted to throw them out he put them back inside for when people weren't watching. He looked around and sighed, no one had bothered to give it to him in person, no one had the guts to do it or he just wasn't good enough. "Hand it to me or don't bother." He muttered as he closed the locker door and started away.

"Hey Dean!"

He looked toward the higher pitched voice and smiled as a few girls scurried over to him, "Ladies, good morning." The Winchester charm was on and at full blast, the half smirk-smile, cheeky tone of voice, half-lidded eyes, and even a slight bit of eyebrow movement. Dean Winchester wouldn't be caught dead talking to pretty girls without it.

"Happy Valentine's day, Dean." A few of them handed over a card each, but nothing expensive. After all, men were supposed to do the high end shopping right?

"And to you too," His smile was heart melting as he took the cards, "I actually have something for you ladies, as well." The girls giggled excitedly as he secretly reached into his locker to sneak out a few things that others had placed in it for him. He was overly proud of himself for leaving his the lock open overnight for this exact reason. "Here you are," Dean gracefully separate the items and gave one to each girl, all of which were more than happy to even get anything from Dean Winchester.

He'd have been lying if he'd said he wasn't the shit, everyone wanted a piece and that was more than all right by him. Dean gave them a wink before continuing down the hall toward his class, passing by a few people handing out little heart-shaped sweets and snatching a few from the platter.

Valentine's Day, a day for the wicked, a day for the loved, the kind, the lonely, and all an excuse in one way or another. Validation wasn't a word Dean would readily use to describe it but he didn't bother to give it much more thought than that. If someone would ask he'd tell them that Valentine's day didn't prove you were worth anything, that it was just a reason for another person to feel good about themselves for either giving or getting. No one had a pure motive on Valentine's day and that's why he treated is as joke.

Love was real, he'd agree with that. Unconditional? Pure? Healthy? Dean wouldn't have said so.

The day went on and classes passed, people were excited about their plans and Dean had been asked several times what his were. Was he going to go have a romantic evening with someone, ask someone out on a first date, or maybe just go to a club and party? Every Valentine's Day was a different answer between those options, but this one seemed different somehow. Dean shrugged to the last person who asked, looking around the hall for an answer that could help him out. His eyes settled on a bulletin board where a poster had been tacked recently, a pretty little thing that stuck out from the rest with an amazing bit of photography styled with what looked like hand-rendered type.

It read:

"Valentine's Day at The Jar; good company, good entertainment, great times."

"There, I'm going there tonight." Dean pointed at the poster after a quick skim of the advertisement. He just wanted to give an answer but apparently it was now set in stone, judging by the way people lit up about it.

"I've heard about it," Jo nodded with a smile, "The event they're holding started last year and it's a lot of fun, at least worth a few hours. I'm glad they're doing it again."

Dean looked at the poster a little better with a bit of a nod to Jo insinuating he'd heard her, reading quickly to see where it was. "A café," he muttered mostly to himself, 'Well could be in a lot worse places.'

"I'd love to go! Call Jet, maybe he'd enjoy it." She nudged his arm as she made her way down the hall at his side. "Better than going to the bar every year."

"Agreed," Dean smirked and ruffled her hair up, "But I don't know if he'd want to go to a café-"

"It's the one right next to the campus, it's run by a pretty weird dude so during the day it's a café but at night they serve drinks like a bar." Jo informed him as she fixed her do, trying not to grumble about it like a schoolgirl. She was in university, damn it, she should be above all this little sister crap.

"Might be easier to convince him than I thought." Dean grinned, flipping out his phone.

Showing up early was for squares but Dean wanted a good look at the place. It was about 7pm and as Jo had mentioned earlier it was definitely a café but he could see the bar, the stools and the alcohol storage as the barista traded off with a barkeep. It was a very cute little place, Dean noted as he looked up at the walls. There were fine art pieces strewn about, some abstract as hell, there were a few environment pieces and animal paintings but what really got Dean was the photography bits. He hadn't really realized he was a bit of a fan of it until he'd seen the coffee shop's style; whoever their photographer was he had a certain technique. Particularly, Dean enjoyed the silhouette pieces, there was one shape in particular that held his attention; the profile of someone with short wispy hair, a profound nose and jaw, and just the hint of long lashes.

As Dean admired the artwork and the ambiance of the place, he came across the small stage. It almost looked like a shorter version of a runway or a catwalk, the microphone was on a circular piece that stuck out from the rest and further into the crowd. Dean smiled at it and picked a table that would be a great position to see their entertainment for the night. Valentine's day? In a café-bar? The odds were good that they'd get some sexy lady dancing up there and he wanted the best seat in the house.

A waitress went to his side almost immediately, the uniform a cute and slimming kind of piece that Dean thought for sure was vaguely based off a French maid. He gave a smile and ordered a coffee and a piece of pie, it was at least an hour or two before the real fun started, might as well get some pie time in.

Time ticked by, he watched some people trickle in, the workers rushing about to put up the last of the decorations, some of the coffee shop people leave before it got too rowdy, and then finally his friends showed up. The first one in was taller than him, shaggy brown hair and a mean neutral look. That didn't last long, however, as he spotted Dean and lit right up. "Dude!"

"Jet, good to see you." Dean smiled and rose, catching Jet's hand in a quick shake before they pulled each other in for a solid smack to the back.

"You too," Jet grinned as he pulled away and chose a chair, "Been a while since you went back to school, hardly ever see you."

"Tell me about it, guess I forget with everything going on." Dean smiled, about to sit down when he spotted Jo walking in with an older man on her tail. "Jo! Benny! Welcome to the party." He called with a laugh, bowing his head as Benny tipped his hat.

"Shut up, party don't start 'til we walk in." Benny joked, earning himself a smack from Dean on the arm.

"Don't quote bad music, man."

"Noted. So where's the party?" Jo looked around, admiring the scenery and decorations. "It's really nice in here though."

"They'll dim the lights yet," Benny sighed as he lowered himself into his chair, "Gotta set the mood."

Not moments later did the room darken and the bar light up, people already moving to get their first drinks of the night. The chatter grew and soon the room was over taken with sounds of people having a good time, there were couples at the single tables and groups at the larger ones, a few double dates and some even just single people at the counter. And a café worker passed everyone; all given a jar, a pen, and several little paper hearts. Dean looked at the smile on her face and motioned toward his new items, "What're these for?"

"Oh, well it's our Valentine's day event. Everyone writes their names on the hearts and can put a heart in the jar of the people that they like. Winner gets a date night package, movie tickets, and dinner in participating restaurants of their choice." She smiled brightly and motioned toward the pens, "Get writing, there'll be jars to put your names in soon enough."

Jet chuckled and clicked his pen a few times, "Well at least all of our names are fairly short or this'd be a pain in the ass."

Dean smirked, "Yeah, seems kind of stupid doesn't it?"

"Just write your damn name, Winchester." Jo punched him in the shoulder as some sick form of incentive.

Dean listened but didn't see much of a purpose to it, maybe he'd go hit on a few pretty girls and get a free movie out of it. And if the date went well then that would mean sex at the end too, not really much of a gamble. The only problem was he'd be disappointed if he didn't get a lot of hearts in his jar.

However the evening picked up and soon there was too much going on for him to really care about his stupid jar and the paper hearts. It was fun, at first the music was just played from the speakers and there were several karaoke singers to start the night off. People who already knew what was up were wandering around and checking out the different jars they might put their hearts in. The event and evening would officially start in a few minutes and by the look of it there was a man on stage setting up the microphone for their entertainment. Dean smiled; excited for the different possibilities of who he'd get to see up there.

"Hello everyone," A young woman stepped out to speak first, her uniform slightly different from the others. Dean recognized her as the bartender; he glanced over to see a few others were passing out drinks that night. A few people clapped when they saw her on stage, some whistling at her and the general 'she's hot' reaction. "Settle down, single boys." She winked which only got her more attention, "Alright, alright, and ladies!" More cheering for her, the room getting loud and Dean realized that this little coffee bar was actually pretty popular. He wondered why he'd never come here before.

"Okay, okay. Let's get on with this game, shall we? For those of you who are new to this, you were all given a few things when you got here. The jar is yours, hold onto it because you're gonna need it to win. Everyone was given ten hearts; you need to put your name on them for them to count, okay? The point of this is to put your hearts in the jars of people you like, the person with the most hearts with names on them at the end of the night gets the date night prize."

Jet smirked and looked over at the others, "If we really didn't care we could pool our ten in one person's jar and we'd be done with it."

"You don't know that it'd work. Besides, this sounds like fun." Jo smiled and looked around the bar.

"And I guess we've left you all waiting for too long, haven't we? Let's get our entertainment out here! Tonight's a treat for all of you, by much request Valentine's Day this year will be sung by Castiel Novak! Let's give our beautiful babe a round of applause!"

Dean couldn't say he wasn't intrigued by the name, Castiel? It was so different, exotic. He sat up in his seat as the curtains moved to reveal the band set and the lights behind them silhouetting the figure coming forward. That quickly vanished to reveal a trim man in a fitted suit. It wasn't even one of the plain suit and tie kind of things either, the colours matched, there were extra pieces to the suit like a vest and other things that Dean couldn't ever name if he tried. This guy looked sharp, it reminded him of something Jo had said once about women in lingerie and men in fitted suits.

Only for a moment Dean fooled himself into thinking this person wasn't gorgeous, this man couldn't possibly be beautiful or catching. But whom was Dean kidding? Everything about his walk caught the eye; the slight sway of his hips and shift of his back was subtle but provocative. He reached the mic and shook the bartender's hand. "Thank you, Rachel."

Dean nearly melted in his seat from the voice, staring up as this Castiel turned toward the room of people. That face, those eyes, he was beautiful.

"Good evening everyone! Let's give Rachel a round of applause, thank you Rachel." He'd taken the microphone from her so elegantly, his voice was smooth and had the hint in it that he could be as rough and tumble as anyone else. As the clapping subsided he smiled out at the patrons and Dean swore he'd lost the feeling in his legs. "Ladies and gentlemen, thank you all for choosing me tonight. And if you didn't then let me show you why you're wrong."

"He's cute," Jo whispered, earning a shrug from the guys at her table aside from Dean, which only caught her attention.

"Let the event begin, and I'll start it off with something slow, we'll be taking requests throughout the night so come on up and we'll see what we can do. In the meantime we'll be covering Alanis Morissette's 'Head over Feet'." As the band started to play and Castiel began immediately.

"I had no choice but to hear you.

You stated your case time and again.

I thought about it."

Dean couldn't think of anything as he listened, watching the way Castiel was so into the music, the song and the feeling of the room. He wasn't going to sing any of the douchey songs where they go on about how hot someone was, he was singing love songs. And the way he did it, he really believed what he was singing, or at least he was really good at putting the passion into the words as if he were truly in love with whomever the song was meant for.

"You've already won me over, inspite of me.

An' don't be alarmed if I fall, head over feet.

An' don't be surprised if I love you for all that you are.

I couldn't help it,

It's all your fault."

Castiel had looked throughout the crowd and Dean could have sworn they'd locked eyes, like Castiel was staring into him and connecting with him. Like maybe Dean was the person this love was meant for.

"Dean?" Jo nudged him and snapped his attention back to the table. "You paying attention?"

"Yeah, sorry. What happened?" Dean turned to look at everyone, trying to ignore the smirks on their faces.

"Just talkin' 'bout you." Benny glanced at Jet who only smirked in return.

"Come on, let's enjoy the evening." Jet lifted his bottle, "To every sad soul at home drinking alone, this is for you guys."

"You're an asshole." Jo kicked him under the table, barely getting a reaction.

"And you're abusive." Benny smiled and clinked glasses with Jet as the others did the same.

The evening continued on and several times people came up with requests, love song after love song. Castiel had stepped down to let someone else take the stage to say something to their girlfriend or boyfriend. When he came back he started with another song that Dean had the free moments to listen to, a cover of Alicia Keys' 'Fallin'' and Dean couldn't believe the vocal chords on this stunning man. With every song, cheesy, dorky, or otherwise, Dean could feel something slipping.

And with enough alcohol in everyone's systems it no longer mattered what was going on. The others had scooted off to talk to people to fill their jars, hoping maybe they'd win the prize. Dean didn't care; he would have much rather sat and watched this apparently famous café performer sing his heart out to the love struck patrons of the bar. Dean's mind had protested to this, staring at a man when there were beautiful women to hit on. But again, the more alcohol he drank the less it seemed to matter. And even then he hadn't been drinking all that much, it was just the atmosphere of the place. Everyone was giving everyone hearts and hurrying about to talk to almost everyone.

Dean's jar was already pretty full but it was nothing compared to the jar that sat on the stage at Castiel's feet. It was nearly over flowing and after each song Castiel had to bend over to smush the little paper hearts further down. This time when he did Dean called over from his seat, which was right in front of the stage so he was easy to hear. "How about Everlong by the Foo Fighters?"

Castiel looked up and Dean felt a jolt in his spine, an awkward little smile coming to his lips to try and show confidence. "You got it, baby."

Dean felt his mouth go dry as the music started up, something a little older and a bit of a different beat than the other songs that had played. Castiel had a beautiful voice and he did the song justice, Dean had lost himself in it all as the song played out.

"And I wonder,

When I sing along with you;

If everything could ever feel this real forever.

If anything could ever be this good again.

The only thing I'll ever ask of you,

You've got to promise not to stop when I say when."

The song ended and Castiel took a slow breath, "Alright everybody, that's it for me tonight! Thank you again, I love you all. Everybody have a good night, stay safe."

Dean felt a little empty to watch Castiel leave the stage, taking his little jar with him. And then Dean realized he hadn't put his hearts anywhere, but who to give them to? Well Castiel seemed to be the only person to catch his attention so they should go to him. Dean's decision was quick, to the point, and entirely naïve. He hadn't realized that being face to face with Castiel would bring anything out in him, and yet there he was, struggling to get to the bar where the singer had taken a stool.

"Hey stranger," Dean said as he leaned over Castiel's side, catching the other man slightly off guard. "You got room in your jar for my heart?"

For a second those blue eyes just blinked and stared at him but soon Castiel's face cracked a smile and he laughed, openly and outwardly laughed at Dean. "Oh! Oh my god!" He wheezed for a breath as Dean stole the bar stool next to him, "That made my night."

"Well I'm glad I could return the favour." Dean turned on the charm to the best of his abilities, not overly dramatic or cheesy but enough to keep Castiel's attention. "You sing here often?"

"Every Friday night," Castiel's smile stayed though it had grown a little subtler. Beautiful really was the only word that Dean's mind could produce to describe him. "You enjoyed it?"

"Very much, you have a beautiful voice." Dean was glad he managed to get the word out.

"Thank you, what's your name?" Castiel eyes glanced down for a second before snapping back up to meet his and Dean felt his tongue go numb.

"I'm uh… Dean, Dean Winchester." The slight stutter seemed to bring a laugh out of the other man who finally got his first drink of the night.

"Well Dean, it's a pleasure to meet you." Castiel tipped his head before taking a swig from his beverage, something a little fancier Dean noticed.

"Likewise."

The floor was cleared of tables and the music started to play louder, more upbeat and people started to move onto the dance floor that had been prepared. Castiel looked over there with that half smile, just quietly observing things but it was enough of an opening for Dean to take the hearts from his pocket and place them all in Castiel's already full jar. The blue-eyed stranger hadn't missed the gesture, however.

"For me?" He looked up and Dean was surprised to see even a hint of shock there.

"Yeah," Dean grinned, starting to feel cocky in the fact that Castiel seemed to be giving him more attention than anyone else.

Of course that was somewhat short lived when a few girls came to get a picture with him. Castiel of course couldn't say no, his sweet demeanor, Dean realized, wouldn't allow it.

'He's… such an adorable guy.' Dean felt his pulse quicken as Castiel smiled in the quick little photos, one after another because more people came to do the same. A few autographs because it seemed polite to do it. Dean couldn't believe he hadn't heard about this place sooner, though a Friday night is when he would have been in a bar or a club, not in a supposed café right outside the campus grounds. "Looks like The Jar is my new favourite Friday night hang out," He mused with a smirk.

"Really?" Castiel raised an eyebrow as he sat down again, surprising Dean a little. Castiel wasn't supposed to have heard that. "You aren't bothered by the fact that we do covers?"

"I'm serious, and it doesn't bug me. Why reinvent the wheel, right?" He knew it wasn't the same when it came to music but it seemed to get Castiel's smile back. "So I have a question for you."

"Shoot, Romeo."

Dean chuckled and shook his head, leaning forward a little more seriously he said "You have any raisins?"

Castiel made a face, his nose scrunched up and eyes narrowed, brow furrowing as he tried to make sense of the question's possible meaning. "Uhm… no?"

"No? Then how about a date?" Dean waggled his eyebrows as Castiel immediately caught on to the pick up line.

"You are terrible, Dean Winchester!" Castiel laughed and turned away, his smile wide from ear to ear. He glanced at Dean who only wiggled his eyebrows a second time to suggest the same, getting another laugh out of the singer. "Alright," Castiel conceded evenly, an air of confidence and excitement about him. "A date it is, let me give you my number."

And even as they counted everyone's hearts that night, even when it was all over and Dean had that number in his phone, he was still dumbstruck. He'd just asked out a man, a performer, a locally famous singer named Castiel. And Castiel was classy as fuck, as Dean had come to know over the course of their evening. Classy, alluring, graceful and kind, Castiel managed to show all these things in the span of an hour or two.

All of those things and more, and Dean had stepped out of his beliefs and comfort zone to ask him out on a date. Of course, Castiel won the prize at the end of the night, which meant a movie and dinner. When he went up to receive it he looked directly at Dean with a wink but that was all the public awareness that got out.

"Figures," Jo smiled, "of course the guy singing for us all night would get the prize. They shouldn't let the staff play."

"He volunteers, actually." Benny shrugged, "From what I hear anyway."

"No kidding?" Dean looked over, "So he's got a second job then?"

"Dunno, I just know that he's related to the guy that owns this place."

Dean looked down at his phone and the number it held, the name spelled out in the same typeface as everything else even though Dean felt like maybe it should be more unique. More like the man he'd just met. But that was probably just the alcohol talking. He was sure he'd regret this decision in the morning.

Author's Note:

This story was a request by PlotBunny2468. I do not own anything that was mentioned here, characters or songs or whatever you might be concerned about.

The chapter lengths will probably mostly be half this size but this one I felt like it needed a bit more weight to it. (That's usually how I do it I think, the stories start with a long chapter or they start really short). But anyway, please review and let me know what you thought :)