I do not own TVD or TO

Consider this my Valentines Day gift to y'all. In my head this takes place around the start of February. The entire story will encompass the span of a week and maybe have an epilogue.

I'm planning now for 4-5 chapters: 2 dates with 2 guys, the final choice, and an epilogue.

Chapter 1: The Bet

Chapter 2: Pick-up Lines

Chapter 3: The Date Part 1

Chapter 4: The Date Part 2

Chapter 5: Choices

Chapter 6: Epilogue

"You have absolutely no game," Kol smirked. Taking a swig from his drink he slammed the glass down on the table and waited for the coming rebuttal.

"I beg your pardon," Elijah sputtered on his bourbon. He was already regretting the decision to join his younger brothers for a night of drinking.

"I believe he was referring to your sexual prowess," Klaus chuckled. Reaching for the bottle he replenished their drinks. "Exactly how long has it been?"

"That is none of your business," he glared at his siblings. Never before had he wished for a mountain of paperwork to be buried in.

"That's code for he doesn't know," Kol snickered. He cast Klaus a knowing look. "I told you, Nik. He's got no game."

"While I fully object to your terminology, I can assure you that I do, indeed, have 'game'," he grimaced, eyes flickering over his brother. "I however prefer not to discuss such things."

"I don't believe you," Kol cocked an eyebrow.

"I do…"

"Prove it," Kol grinned.

"Just when I think you're starting to grow up," Elijah rolled his eyes.

"Come on, 'Lijah," Kol leaned over the table, "take the challenge."

He tilted his head, intrigued at the prospect. He had always been competitive and his siblings knew it, but it had been a long time since he had accepted one.

"What would this challenge be?" Rebekah slid into a chair beside Klaus. Her eyes darted between her brothers quickly as she waited for one of them to answer.

"I'm issuing a bet," Kol turned to his sister, "that I can get a woman into bed before our noble brother here."

"That is so juvenile," Rebekah heaved an exasperated sigh; it was just like Kol to come up with something like that.

"Does that mean you don't want to participate?" Klaus chuckled.

"How, pray tell, would I be participating?" Rebekah cocked an eyebrow. "Am I also being issued this challenge? Because if I am we both know they'll lose," she nodded to Kol and Elijah with a smirk.

"We all know you can out seduce any of us," Kol rolled his eyes, "so no, sis, you will not be included in this challenge."

"But you can help pick the object of their attentions," Klaus winked. He had very nearly used the word 'target' but he had known he would have gotten an earful from his sister for that one.

"I have not agreed to this yet," Elijah pointed out.

"You will," Kol smirked, "because if you win I'll sign over the deed to the vineyard."

"And in the nonexistent event of my loss?" Elijah prompted.

Kol tilted his head and considered, although the prospect required no extraneous thought. When their parents had passed property had been divided up equally amongst the siblings, but Elijah had gotten something he wanted.

"Mother's books," he cocked an eyebrow. They should have gone to him anyway since he was the only one who could utilize them.

"It would appear we have a wager," Elijah smirked.

"Fantastic," Klaus grinned gleefully. "Now obviously there has to be a time limit on this…"

"… and the same woman," Rebekah added. "It doesn't prove anything if you each choose a different person."

"And we will be choosing," Klaus motioned to his sister. "What do you think, Bekah: a week?"

"Sounds reasonable," Rebekah nodded, "but if neither of you are up to the challenge then Nik and I get profits."

"I'll take the vineyard," Klaus took a swig from his glass.

"That's good, because I want mother's books," she smirked. Her eyes moved to her brothers' inquisitively. She turned her gaze towards the rest of the bar when they agreed, scanning for the perfect woman.

A slim redhead laughed over the music as she placed her hand on a man's chest. Her coy smile was promising, but there was madness in her eyes that Rebekah knew would find a potential partner in Kol. Those two would literally paint the town red before falling into bed together ensuring the rest of the siblings lost out on the bet.

A woman with wavy hair that fell to her shoulders was leaning on the bar. Her clothes and eyes suggested she was looking for a hookup, and the way the brunette was eyeing Elijah made it seem like she would willingly go home with him; she'd probably sink her claws in and never let go.

Rebekah shook her head minutely. There was no way she was going to make this easy for them. Just when she was about to give up on someone inside she spotted a duo by the bar. Both women were undeniably attractive, but her choice was made when she sensed Klaus' eyes on the blonde; it was clear from the straightening of his spine that her brother had seen and taken an instant liking to her.

Rebekah instead scrutinized the brunette. Her complexion was olive and the perfect contrast to her wavy brown hair. A blue dress fell to the middle of her thighs and was covered with a supple leather jacket. She was the classic girl next door; it was evident in her easy smile.

She knew nothing about the brunette, but she had a feeling seducing her would not be an easy task. Mainly because it was clear she was not out looking for a hook-up; the brunette had come out in search of a fun evening with a friend.

"Her," Rebekah pointed. "Step one: get her number."

It had been a very, very, long week. First she'd had to deal with flaky authors who couldn't be bothered to deliver their stories, making her boss angry and by extension making her life a mess. Then, her co-worker had decided to rub in the fact that she just couldn't do anything right and to plaster an embarrassing picture of her all over the office. Seriously, she wasn't that clumsy, but Tessa was just so particular about her coffee, a non-fat half-café soy latte with a dollop of whipped cream and a handful of chocolate sprinkles; she had to have it every day at nine o'clock on the dot. One little trip and suddenly that non-fat half-café soy latte with a dollop of whipped cream and a handful of chocolate sprinkles was all over her pristine white blouse.

Naturally Hayley had been there to capture the moment on film. She'd been gunning for the same job as her for months.

"I seriously don't know why you haven't quit," Caroline took a sip of her apple martini.

"It's a stepping stone," Elena shrugged. She bit back her moan when the screwdriver hit her tongue; she had been in serious need of that drink.

"You've been saying that for years," Caroline rolled her eyes. "The only stepping stone I see in that job is you. You let that bitch walk all over you."

"I do not," she couldn't quite meet her friend's eyes. There was never anything she could hide from her roommate; they had been best friends since high school.

"You do," Caroline insisted. "We are literally standing off to the side, avoiding the empty stools, because she is there."

"I just don't want to deal with her," Elena sipped her drink. She shifted so her back was to Hayley and focused on her friend.

"You don't want to deal with the ass-kissing bitch that is your rival assistant, or the boss who might as well be the creature from the black lagoon." Caroline rolled her eyes. "Seriously, 'Lena, you need to quit."

"No, Care," she sighed, "what I need is the money."

"Freelance," she shrugged.

"If I do that it's only a matter of time before I blow through my savings and can't make rent," Elena tilted her head and smiled.

"Or…" Caroline drew out the word, "… you send out that novel you finished and get recognized for the literary genius you are. You can write articles in the meantime."

"I'm not a literary genius, Care," she shook her head; "I'm just an assistant with editing aspirations."

"You're a writer," she fixed her friend with a look. "You've got a degree in journalism, and you've written a novel, a couple of children's books and several short stories; all of which are more than ready for publishing."

"In case you're forgetting I did show some of my work to Tessa. Her reaction was to sneer and tell me to come back when I had more experience."

"Tessa is a bitch who wants to belittle you and keep you as her overworked personal assistant." Caroline groaned. "She can't do that if you become a best-selling author."

"I thought you were the bitch that wanted to belittle me?" Elena smirked.

"Don't be ridiculous," Caroline scoffed, "I'm the bitch that loves you and wants to see you succeed and reach your dreams."

"That's oddly sweet," Elena's lips quirked up in her easy smile.

"Don't look so happy because you won't like me tomorrow when I make you send out those manuscripts," Caroline pointed to her, "but tonight I am your best friend. I'm the friend who knows exactly what you need."

"Oh," Elena laughed softly.

"Yup," she popped the 'p'. "You need to drink a lot and flirt; which works out wonderfully because there are two insanely hot guys who are totally checking you out right now," she shook her head softly, "don't look. Use the mirror."

Elena followed her instruction and glanced in the mirror over the bar. At a table off to the other side of the dance floor sat four people: three men and a woman; they all resembled each other in a way that suggested they were either cousins or siblings. The two men with dark brown hair were indeed checking her out.

"Maybe you can have a three-way," Caroline waggled her eyebrows suggestively, "with the smoking hot brothers."

Elena very nearly choked on her drink.

"There is no way I am going there again," she glared at Caroline.

"That was totally different," the blonde rolled her eyes, "and so not your fault. How were you supposed to know that Damon had a secret thing for you?"

"He agreed to have a threesome with his brother," she deadpanned.

"From your retelling of the evenings in question I'm fairly certain all of the focus was on you," Caroline smirked.

"Precisely," Elena sighed, "and it nearly tore them apart. Do you know that Damon showed up on my doorstep not two hours after I broke up with Stefan, convinced I did it because I wanted him?"

"Yeah," Caroline snickered, "I was there, remember? I was in the living room laughing my ass off."

"And after the disaster that was Damon and Stefan I went on a bit of a bender."

"I recall," Caroline tilted her head. She could feel the eyes of the third man on her and was not overly opposed to his attention. "You went a little sex crazed."

"I was not sex crazed," Elena rolled her eyes. "I was only ever with Stefan, and then Damon."

"And then four other people in the span of a month," Caroline deadpanned.

"It was a sexual awakening," Elena blushed. "I rebounded… several times."

"With two women," Caroline's eyes twinkled with amusement.

"I was curious," Elena shrugged.

"And now?" Caroline prompted.

Elena glanced at the mirror again and the table where her admirers were situated. Her eyes flickered over each face quickly before she hummed quietly.

"Now… I think the blonde's cute."

"Would that be the guy or the girl?" Caroline's eyes narrowed.

Elena bit her bottom lip to stifle her smirk and met her friend's eyes.

"Both, but judging from the way he's looking at you I don't think he likes brunette's," she teased. "Her, though…"

"She's totally checking you out," Caroline giggled. The alcohol was starting to get to her head.

"How would you know?" Elena laughed. "You my friend have no gaydar."

"Maybe not," Caroline agreed, "but even I can tell that she is staring at your assets." The blonde straightened when the younger man stood from the table.

"Hot guy, twelve o'clock."

What's the cheesiest pickup line you can think of, or that has ever been used on you? Because I think Kol would lead in with something overdone for the sole purpose of making a girl laugh. Then I need something a little more suave for Elijah.