Disclaimer: So there's 319 n's and 335 o's in this story... so I guess subliminally I've said 'no' 319.16 times...

A/N: Howdy doodle peoples! It's 1:15 in the morning and I still gotta memorize something for theatre tomorrow morning, so I'm going to make this quick... today's one shot is one of my few attempts at humor. And you'll see why very quickly... it's my vane attempt at making you all smile, or possibly, if I'm lucky, laugh. It's also a long ago request fic of Dean getting rejected. One last added note-- this one shot is dedicated to one of my best friends; Karlea (haha.. yeah, it's her name in here, but I wrote it the way it's actually pronounced). She was encouraging me and laughing at this story the whole time... and she's never seen an episode of Supernatural... Anyways... I got some memorizing to do, and you all got some reading to do-- enjoy!!

Title: Angst Break!
Genre: my immensely horribly written humor...
Summary: Dean bets Sam twenty dollars that he can get the number of any person in the bar...

Angst Break!

"Five bucks."

"Twenty."

"Ten."

"Fifteen?"

"Deal," Sam laughed as he leaned back in the bar stool, stretching his long arms up into the air in an exaggerated stretch.

"Dude, do you doubt my abilities so much, that you're willing to bet me fifteen dollars?" Dean questioned between two large swigs of his beer.

"No, I doubt your abilities so much that I was willing to bet five dollars," Sam corrected, "You were the one who insisted on fifteen."

"Fine--" Dean finished off his beer and placed it forcefully on the counter behind his brother, "Point out any woman in this bar Sam, and I guarantee that I'll be able to get her number," the elder pulled a crumpled twenty from his pocket, "Twenty bucks says so."

"I said fifteen," Sam's significant sobriety over his brother was evident.

"And I said twenty," Dean paused, "And I'm older, so that means we have to listen to me."

Sam grinned and snatched the twenty out of Dean's hand, "Alright hot-shot," he pointed to a lady standing near the dance floor; her curly auburn hair flowing down halfway her back, "That girl there."

Dean returned a drunken smile, "Watch me."

"Oh I'll watch all right," Sam smirked to himself as he watched his brother stumble off across the floor.

Sam slid off the stool and followed Dean closely behind; eager to not only hold the twenty that sat in his hand, but also to see his almighty big brother make an ass out of himself. Something the eldest Winchester did often, though rarely in public.

"Hi," Dean flashed his charming smile as the woman with the long hair turned around, "Name's Dean."

"No, actually, my name is Karlee," the lady smiled slyly.

Dean chuckled, "Right. So… Karlee… you come here often?"

Sam covered his mouth to stop the laughter coming through; this was going to be far more entertaining than he could have ever hoped for.

Karlee eyed Dean a long moment, "Not anymore."

"Ouch," Dean faked hurt, "How 'bout I buy you a drink-- see if we can change your mind at all?"

"Sure," Karlee's attitude dramatically changed as she hooked her arm around Dean's, "Dean, did you say your name was?"

"That's right," Dean leaned over and seductively kissed her neck as they reached the bar; Sam following a slow distance behind, "So, what do you drink?"

"I have very expensive tastes," was all Karlee replied.

Two drinks and over fifteen dollars later, Dean stared charmingly at the lady beside him. Or with what he thought was charm. Sam had to turn away as his own drink spurted out of his mouth with laughter. Wishing dearly he had a camera on him, Sam turned back to the scene just in time to hear Dean try one of his more famous lines out.

"So Karlee," Dean raised one eyebrow, "I'm actually here from a small production company, and am trying to find some woman that are just perfect for a part…"

"Oh?" Karlee took a sip from her drink, "And what kind of part would that be?"

Dean did a quick scan up and down Karlee's body, "Well we can start with your eyes, and then work our way down to--"

"How about," Karlee quickly interrupted as she placed a single finger on Dean's lips, "you buy me another drink first?"

"Any chance your taste has… cheapened?" Dean asked hopefully.

"Only if yours has."

Again Dean bought another expensive drink, though this time caught a glance of Sam who gave an enthusiastic thumbs up. Not only was Dean's own alcohol starting to kick in even more, but the room seemed insistent on continual movement even after Dean put down his bottle. On this note, Dean realized he should hurry with the bet before he forgot what it was.

"So," tact was slowing as fast as Dean's speech, "Do you have a number I can reach you at Karlee?"

Karlee studied Dean a moment, "A number?"

Dean took another swig of his beer, "Yeah. You know-- for the phone."

"Oh," Karlee smirked, "Right. I'll be right back."

"Sure thing," Dean leaned in for another tasteful kiss, but quickly found himself nearly falling flat on his face as Karlee moved from her seat.

Sam made quick movement to catch Dean before he did take the header, "You ok?"

Dean grinned, "Perfect. I have her just where I want her."

Sam forced back a laugh, "On the other side of the bar?"

Dean glanced back to where Karlee was talking with the bartender, "She'll come back."

"Alright hot-shot," Sam helped Dean to sit more securely in his chair, "Just make sure you stay away from the kissing at this point because you're breath is horrible."

Dean crinkled his forehead, "It is?"

Sam smiled and clapped Dean on the shoulder before moving back to his seat, "Yup."

Just as the drunken Winchester claimed, Karlee came back to her spot beside Dean and sat down. She smiled widely before taking a sip of her drink.

"Welcome back," Dean smiled.

"Miss me?" Karlee winked.

Dean opened his mouth to respond, but paused slightly before doing so, "No… not really. I could see you the whole time."

Karlee bit back a retort, "So… you said you were a producer?"

"Yeah," Dean nodded, "But I'm going to need to get your number…" he forced a drunken smile, "For callbacks."

"Ok," Karlee nodded as she leaned in close to Dean's ear and whispered, "But how about another drink first?"

Dean raised his hand to the bartender who brought over another expensive drink and placed it in front of the increasingly beautiful woman. Ready for his triumphant win, Dean took another large gulp of his beer to finish it off, and placed it on the counter.

"So," there was no hiding his inebriation, "How about that number?"

A large grin came to Karlee's face as she lifted a phone book up from her lap and plopped it in front of Dean, "Here you go hot-shot. It's in there I swear… just keep looking."

Dean stared dumbfounded at the thick book as Karlee smugly got up from the seat. With a spin of the heel and a smile on her face, Karlee walked over to where Sam was sitting a few seats away.

"Thanks Karlee," Sam grinned and held up the twenty dollar bill.

Karlee took the bill and spoke before walking to join her friends back on the dance floor, "Any time Sam."

The End.