Bartenders and Breakups

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Rocky's Bar. A small but sophisticated place that had the best burgers and the hottest bartender in town.

It was a small town, so Dean Winchester, certified hot bartender, usually knew everyone that turned up. There was Bobby and Rufus, the old drunks who turned up every weekend to argue over everything, down a bottle of whiskey, and then make a bet, with the loser paying the bill.

Then there was Charlie, the nerd who always looked slightly out of place in the bar. But she'd show up like clockwork in her glasses and Star Wars T-shirts, writing frantically on a notebook or typing away on a computer. She had the biggest crush on one of the waitresses, so Dean always made sure Jo waited the table, hoping to nudge the two girls together. 

Then there was Ash, the hustler who came in, downed half a bottle of rum, and would cheat even drunker people out of their cash in a game of pool. Dean usually kept a close eye on him, but Ash knew better then to try and swindle anything too big past Dean.

Dean knew everybody, customer or worker. Benny and Garth worked the kitchens, Jo, Pamela, and Ellen waitressed and ran the front of the house, and Dean worked the bar. He had an art to fixing drinks and knowing exactly what people wanted, and what they needed.

But when a new guy stumbled into the bar one Saturday night, Dean was at a loss.

He was a handsome guy, with blue eyes and dark hair. His suit was rumpled up and he slumped into a seat at the bar, sniffling and looking like somebody had just run over his dog.

"Hey buddy," Dean offered. "What can I getcha?"

"Something strong." Mystery man demanded. 

"Any other specifications?" Plenty of things at the bar were strong.

"No, I don't know." The man rubbed at his face, his voice wavering. "I don't even know what I'm doing here, I hardly ever drink." 

"It's alright." Dean got the poor guy a glass of water. "Why don't you start with this." He looked up, grateful, and Dean took in a breath. Damn, was this guy handsome. "So, what's got you down?" He asked.

"My girlfriend dumped me," He explained.

Damn. Mystery guy didn't play for his side of the field. Ah well, maybe Pamela would end up leaving with a new friend.

"Oh?" Dean questioned, waiting for him to elaborate. The bar was reasonably crowded, but everyone else was fine at the moment. Dean had the time for a chat.

"Yeah." He sipped the water. "We'd been dating for three freaking years, and she ditches me tonight for some British dude."

"Ouch." Dean winced. 

"It's fine. She was a jackass anyway." He sighed. "Stupid Meg."

"You deserve better," Dean declared.

"How do you know? You don't even know me."

"True, but I'm a bartender." Dean grinned. "I'm good at reading people, and it looks like you didn't deserve a jerk like her."

"It's probably my fault anyways," He offered. "I should know better then to date girls. Nothing but drama and betrayal. I should go back to guys."

"You like guys too?" Dean asked. So he did have hope!

"Pan." He explained. "So I don't really care."

"I know what you mean," Dean offered. "I'm bi."

"No way." Mystery man's eyes widened. "A hot guy like you could be into dudes?"

"Yep." He smirked. "You seem a little better. Up for some alcohol?"

"You got Sam Adams?"

"You bet."  Dean cracked open a beer and handed it to him. "I'm Dean, by the way."

"Cas," He replied, taking a swig of the beer. "You always this friendly as a bartender?" Dean shrugged.

"It's a small town. Most of these folks are regulars, so I make conversation. Ask how things are going because I know what's up with them."

"Yeah?" 

"Yeah. But you're new, so I guess I get to learn about somebody different for a change." Cas smiled.

"Well you've got the basics." He declared. "Cas, fresh off a break up and ready to get wasted."

"Cas," Dean corrected. "Hot and heartbroken."

"That sounds like a Sleepless in Seattle sequel."

"Sounds like a great movie." 

Dean learned a lot more about Cas by the time closing time rolled around. And by the time he got the full story, he too was ready to go and knock some sense into Cas's ex-girlfriend. 

But then the bar closed, and Cas stumbled home why Dean stayed behind to close up.

"I saw you made a friend," Jo commented. "Maybe more?"

"Nah," Dean offered. "He just broke up with a girlfriend."

"Damn, I knew he was too hot to be gay."

"No, he's pan."

"So you've got a shot." Dean smirked.

"Yeah, sure. He'll probably never come in again."

Dean was wrong.

Cas started to become one of the bar's regulars, showing up like clockwork, and always sitting at the bar to chat with Dean. The bartender helped him off his break up and back on his feet, and soon Dean found himself being a little flirty towards the man. And Cas didn't have a problem being flirty right back.

"Hey," Cas asked one night, as Dean was cleaning off a glass. "What time do you get off work here?"

"Usually around two," Dean admitted. He stayed until after last call, and then closed up on weekends.

"You got any fun plans for after work?" Cas questioned. Dean smirked.

"No," He admitted.

"Well uh, you wanna hang out after?"  Dean grinned.

"Sure."

Cas hung around until Dean closed up the bar, and they walked out together.

"What do you want to do now?" Dean questioned, breathing in the night air. It was a gorgeous night out.

"Up for a walk?" Cas asked.

"Okay," Dean grinned. 

"Great," Cas smiled. "I'll show you my favorite spot in the city." They walked for a while, talking more, hands entwined, until they ended up in a little park. It was dark out, the path only lit by old street lamps. They ended up sitting on the edge of a stone fountain, looking up at the stars.

"It's beautiful here," Dean commented. Cas smiled.

"I'm glad you like it." He declared. "This is usually where I go, whenever I need to clear my head."

"You ever bring anyone with you?" 

"No."

"Not even Meg?" Cas wrinkled his nose.

"Definitely not Meg. She could never appreciate a place like this." Dean smiled. There was something about the fact that Cas trusted him with this place. It was nice.

They started dating officially after that. Cas would turn up at the bar most nights, just begging from a kiss from the bartender. He'd play Dean's favorites on the jukebox and laugh as he danced around the bar, fixing drinks and talking with folks.

They stayed after closing a few times, dancing, splitting a drink, kissing, or just plain talking.

"Would you kill me if I played a song that wasn't classic rock?" Cas asked one night after closing, when it was just the two of them left in the bar.

"As long as it's not utter trash, I'm fine with it." Dean declared, sitting up on the bar. Cas clicked on a song and climbed up on the bar.

"I thought it was relevant to us." He explained, holding out a hand.

"Oh, so we're dancing ON the bar now," Dean commented, taking his hand and standing on the bar. "You scratch my bar, I'll kill you." Cas laughed.

"I won't hurt the bar, I promise."

"And don't fall off either."

"That goes for you too." The song got louder, and Dean smirked at the lyrics, dancing with Cas.

This is a shout out to my ex
Heard he in love with some other chick
Yeah yeah, that hurt me, I'll admit
Forget that boy, I'm over it
I hope she gettin' better sex
Hope she ain't fakin' it like I did, babe
Took four long years to call it quits
Forget that boy, I'm over it


Dean laughed as Cas sang along 

Guess I should say thank you
For the hate yous and the tattoos
Oh baby, I'm cool by the way
Ain't sure I loved you anyway
Go 'head, babe, I'mma live my life, my life, yeah


They jumped off the bar and hit the hardwood floor, and Dean pulled Cas close, spinning him around on the floor as they grinned and laughed. 

Shout out to my ex, you're really quite the man
You made my heart break and that made me who I am
Here's to my ex, hey, look at me now
Well, I, I'm all the way up
I swear you'll never bring me down
Shout out to my ex, you're really quite the man
You made my heart break and that made me who I am
Here's to my ex, hey, look at me now
Well, I'm, I'm all the way up
I swear you'll never, you'll never bring me down
Oh, I deleted all your pics
Then blocked your number from my phone
Yeah yeah, you took all you could get
But you ain't getting this love no more
'Cause now I'm living so legit
Even though you broke my heart in two, baby
But I snapped right back, I'm so brand new, baby
Boy, read my lips, I'm over you, over you, uh
Guess I should say thank you
For the "hate yous" and the tattoos

Oh baby, I'm cool by the way
Ain't sure I loved you anyway
Go 'head, babe, I'mma live my life, my life, yeah


They jumped around, goofing off and laughing.

Shout out to my ex, you're really quite the man
You made my heart break and that made me who I am
Here's to my ex, hey, look at me now
Well, I'm, I'm all the way up
I swear you'll never bring me down
Shout out to my ex, you're really quite the man
You made my heart break and that made me who I am
Here's to my ex, hey, look at me now
Well, I'm, I'm all the way up
I swear you'll never, you'll never bring me down
You'll never bring me down
Shout out to my ex, you're really quite the man
You made my heart break and that made me who I am
Here's to my ex, hey, look at me now
Well, I'm all the way up
I swear you'll never, you'll never bring me down
Shout out to my ex, you're really quite the man
You're quite the man
You made my heart break and that made me who I am
Here's to my ex, hey, look at me now
Well, I'm, I'm all the way up, I swear you'll never bring me down
You'll never bring me down


Shout out to my ex, you're really quite the man
You made my heart break and that made me who I am
Here's to my ex, hey, look at me now
Won't you just look at me now
Well, I'm, all the way up
I swear you'll never, you'll never bring me down
You'll never bring me down


While Cas's ex girlfriend had been a jerk, Dean couldn't help but be grateful for her. Because without her breaking up with him, Dean would've never gotten his Cas.

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