Chapter 1

"Come on Dean, do we have to go to a bar? We should be at the hotel sleeping." Sam Winchester whined to his brother, as Dean pulled into a dirt parking lot and parked the Impala in front of a small rundown bar named Doc's Highway Bar.

"Look Sam, we just finished the case and I'm still jacked up. I need to drink and relax before i can sleep." Dean said, as he got out of the car.

Sam scoffed then said,"no you don't, you just want to hit on girls and hook up."

"Hey hooking up with random chicks relaxes me."

Sam rolled his eyes before saying,"fine we'll go in here, but only for a few beers. I'm tired."

"Whatever you say Sammy." Dean said, as he opened the door and walked in like he owned the place. He bit his bottom lip as he looked around the room at all the hot girls.

"This is going to be a fun night." He thought to himself.

"Alright, let's find a table and get this over with." Sam said, as he stood behind his brother.

"Go grab us some beers and a table. I'll met you there." Dean said, as he walked away from Sam and over to a pretty blond girl in tight clothes.

Sam rolled his eyes again as he walked over to the bar. The bar was in the middle of the room with tables and booths all around it. Sam leaned against the counter as he tried to flag down the bartender.

She was a cute girl, but not the type you would normally see working in a bar. All the waitresses were wearing short skirts and tight t-shirts , lots of make-up and had their hair styled. This girl was wearing a pair of fitted blue jeans and a loose fitted t-shirt. Her brown hair was pulled back in a low ponytail, she was also wearing a pair of black rimmed glasses and little make-up.

A few minutes later, she walked over to Sam and stood in front of him before asking,"can i help you?"

"Yeah, two beers please." Sam told her, while holding up two fingers.

She nodded her head as she grabbed two bottles and twisted off the caps then sat them in front of him.

"Anything else?" She asked.

"No, that's all for now."

"That will be $8." She told him.

"You been working here for long?" Sam asked her, as he took his wallet out of his back pocket.

"Yeah about a year now."

"I hope you're careful, it can get scary at night." He told her, he knew the type of things that went bump in the night.

She sighed as she crossed her arms on the counter and leaned toward him before saying angrily,"look mister, I'm not interested ok? Just cause i work in a bar doesn't mean I'm easy. I get so tired of jerks like you, who think they can throw out some lame line and think I'll go home with them. It's not happening."

"Wa-wait no, that's not what i was doing." Sam stuttered.

"Whatever buddy." She said, as she jerked a $10 out of his hand. She quickly rang him up on the register, then handed him back two $1.

"Here's your change, enjoy your beers." She said with a fake smile before walking off.

Sam shook his head as he grabbed the two bottles and walked over to a table. Now long after he sat down, Dean walked over and sat across from him.

Dean grabbed a bottle and took a long swallow then looked at Sam and smiled,"guess how many numbers i have so far?"

"Um, let me think...around i don't care."

Dean rolled his eyes before saying,"don't be jealous cause all the girls love me and i got 14 numbers by the way."

"Lucky you." Sam said sarcastically before taking a sip of his beer.

Dean ignored him as he glanced around the room and said,"i wonder how many numbers i can get before the night is over."

"Who cares."

"Don't be bitter Sammy. We'll get you a girl too."

"I don't want a girl, i want to sleep."

"You're so boring, you need some excitement in your life."

Sam rolled his eyes as he took a sip of beer, he glanced over at the bar, when he saw the bartender a plan begin to form in his mind.

"Hey Dean, i got a idea."

"What?" Dean asked confused.

"Let's make a bet."

"Now that's more like it Sammy, what kind of bet?"

"I bet there's at least one girl in this bar, that you can't get her number."

Dean laughed then asked,"you're kidding right? Look at me, what girl wouldn't want me?"

"Well if you're so sure, then take the bet."

"How much we talking here?"

"$50?" Sam asked with a shrug.

"Sounds good, watch me work Sammy."

"Wait, there's just one rule."

"What?"

"I pick the girl."

"What? Why?" Dean asked.

"My bet, my rules. Plus since you're so confident that shouldn't be a problem right?"

"Right. Go ahead then, pick the girl."

Sam acted like he was looking around the room, but he already knew who he was going to pick. The bartender, Sam was sure she would give Dean the cold shoulder.

"This will be the easiest $50 ever." Sam thought to himself with a smile.

"Find her yet?" Dean asked.

"Yep, her." Sam said, as he nodded toward the bar.

"Her who?"

"The bartender."

"The chick in glasses?"

"Yep." Sam said with a smile.

"Come on Sam, make it hard for me. I'll have that girl wrapped around my finger within seconds."

"If you're so sure, try it."

Dean drank the rest of his beer, then stood up and walked over to the bar. He looked over the girl as he got closer, she was not his usual type. She wasn't a ugly girl, just plain, ordinary and cute. She was the sweet and innocent type that you took home to met the parents, not the type that you take to a hotel and screwed all night.

"What the hell was Sam thinking picking this girl? This is going to be the easiest $50." Dean thought to himself as he leaned against the counter and waited for her to walk over to him.

Once she was finished with the customer in front of her, she looked down at the bar and saw a hot guy leaning against the counter. She sighed as she walked toward him. She knew the type of guy he was, sure he was hot but he knew it and used it to his advantage. She hated those kind of guys.

"Can i help you?" She asked him with a fake smile on her face.

"You can start by giving me your number." He said smiling.

"What number?" She asked confused.

"Your phone number."

"Why?"

"Cause i want to call you."

"Why?"

"To talk."

"About?"

"Whatever."

She grabbed a bottle of beer and twisted the top off then sat it in front of him before saying,"listen, why i don't i buy you this beer, you go over to your friend, have a little laugh then leave me alone."

Dean was in shock as he watched her walk away to help another customer.

"Did she just blow me off?" Dean asked himself with a confused look on his face. Everything happened so fast, he wasn't sure what all happened.

He grabbed the bottle of beer and slowly walked back over to Sam.

Sam tried not to laugh when he saw the look on Dean's face. "So how did it go man?" Sam asked.

"Sh-she blew me off." Dean said, he was still in shock.

"Wow, that's a shocker. Now pay up." Sam said, as he held out his hand.

"No screw that, we're going double or nothing."

"What do you mean?"

"Before we leave this town, not only will i have sex with her, but she will be head over heels in love with me."

"Dean no, we had our fun. Let's leave the poor girl alone."

"No, i know i can get this girl. Plus i love a challenge." Dean said with a smile.

"Come on man, just drop it. Let's go back to the hotel and sleep, tomorrow I'll try to find a new case then we'll leave town and you won't even remember her."

"Oh I'll never forget the girl that turned me down."

Sam rolled his eyes as he stood up and said,"who cares that she turned you down. Now let's go sleep, please."

"You can go, I'm going to say here a little longer."

"Alright look, I'm going to take a cab back to the hotel but promise me something?"

"What?"

"Go hook up with one of the many random girls you met tonight and leave the bartender alone."

"I can't promise that Sammy, sorry."

Sam sighed, he was beginning to feel bad for bring the bartender into their childish bet. He just hoped she could hold her own against Dean. Sam looked over at the bartender and sent her a silent 'sorry' before turning around and walking out the door.

Dean leaned back against his chair and watched the bartender as he drank his beer. He had to think of a way to talk to her, she was to busy at the moment but he knew if he could get her alone she would fall for him. They all did.

"I'll wait for her when she gets off of work." He thought to himself.

He took another sip of beer as he waited for the bar to close so he could make his move.

...ooo...ooo...ooo...

a/n-Hey all, i decided to do another story. I hope you all will like it, thanks for reading and please let me know what you think :)