Elena made her way down the red and green filled aisles, completely miserable. There were people everywhere—buying Santa Claus wrapping paper, debating whether they should get white or colored Christmas lights this year, and worst of all, fighting each other over the last Malibu Barbie doll to buy for their bratty children—she hated it. Elena had hated this time of year for as long as she could remember. To her, Christmas was just a marketing ploy made by big corporations for people to spend all of their hard earned money.

Sadly, there was a reason on why she was subjecting herself to this torture-her roommate Caroline was currently sick and had roped her into buying the supplies for the Police Department's annual Christmas party that she was running. So here Elena was, staring at the fake pine trees in the store that Caroline insisted that they needed because the tree they usually used "looked like it had been run over by all nine reindeer."

She had no clue of which one she should buy. There were ones with pure white pine needles, ones with pretend snow coated on them, ones with lights, and ones without lights. Staring at them gave Elena a headache.

She rubbed her temples and sighed as Mariah Carey's voice came over the radio again. Elena wasn't sure how much more of "All I Want For Christmas Is You" she could hear before she went insane.

Her annoyance for the holiday grew when she felt someone bump into her. Did no one pay attention to their surroundings these days?

The man turned around to apologize. Wow, he had the bluest eyes that Elena had ever seen. Not that that made up for his error.

"I'm really sorry...but, are you okay? No offense, but I've never seen someone look so annoyed while buying a Christmas tree." He told her.

"Not that it's any of your business, but I don't like Christmas. I'm doing a favor for my roommate." Elena said.

"You don't like Christmas?" He sputtered.

"Yes, I don't like Christmas. Goodbye." Elena said matter of factly before walking in the other direction.

She shook her head as she walked away from him. What was with this guy? He was nosy, rude, and rather judgmental. Elena hoped she would never see him again.

Damon shook his head and chuckled to himself as the girl walked away. She intrigued him-there was definitely some fire in those big, brown doe eyes of hers. He hoped that he would see her around some time.

He smiled to himself as he walked around the rest of the store. Damon loved Christmas-the decorations, the music, and most of all the boosted morale of everyone during the season. Well, the boosted morale of everyone but her. He couldn't shake her image from his mind. There was just something about her…

Elena came home empty became overwhelmed by everything holiday related and couldn't take it anymore. At least, that's what Elena tried to convince herself. That man had gotten too much under her skin.

Caroline was lying on their couch surrounded by tissues. It's a Wonderful Life was playing on their T.V. screen, and she saw her friend shed a tear while watching it. Ugh, Elena couldn't stand the movie. It reminded her too much of...she didn't want to think about them. She ignored the movie and looked down at Caroline.

"I'm really sorry, Care. I couldn't pick out a tree. There were way too many options. I think you're going to have to pick it out when you feel better."

Caroline stared at her unconvinced. Sometimes it felt like Care had a sixth sense that could detect lying.

"Is that what really happened?" Caroline asked her.

Ugh, Caroline had caught her. Elena told her the entire story of the rude man at the store.

"Was he hot?" She asked her, excitedly.

"I guess, if you are into nosy men who bump into unsuspecting bystanders and question them on their holiday preferences."

Caroline continued to stare at Elena, and she felt her face flush.

"Ooh, yeah. He was definitely hot."

"Let me get you some chicken noodle soup." Elena said, trying to change the topic.

"Fine, you win this time, Gilbert. But I think you should go ask him out the next time you see this hot, mystery man."

Elena rolled her eyes at her. "There will never be a next time. I am never going to see that man ever again."

Damon stood in line at Starbucks before he went to work. He surveyed the menu, looking at all of the new holiday drinks that they offered. Who was he kidding, of course he was going to get a peppermint mocha like he did every year. He was the next in line to order when he glanced at a girl walking in the door. She had long, brown hair and large brown eyes-it was her. He had a few minutes to spare, he decided. He stepped out of line and joined her in the back.

"You know, I am really sorry about bumping into you the other day. Let me make it up to you." Damon said.

She turned around to look at him and stared in disbelief. "You, again. Are you stalking me?"

"I like to call it fate." He smirked.

They got to the front of the line, and she ordered a black coffee.

"Name for the order?" The barista asked.

"Elena." The girl responded.

"Wow, first you dislike Christmas, and now you are ordering a black coffee. I think you just have an aversion towards joy, Elena." He remarked.

She turned to him and was about to tell him off, but decided against it. She took out her wallet to pay for her coffee when…

"I got it." Damon said, handing the barista his credit card.

"I'm perfectly capable of paying for my own coffee..."

"Damon. My name is Damon."

"Well, I appreciate the gesture, but I am perfectly capable of buying my own coffee, Damon."

There was that fire in her eyes again. Damon simply just smiled at her and ordered his own coffee.

They stood there in silence, waiting for their coffees to be ready. He wanted to get to know Elena more, and find out why she despised Christmas so much. A light bulb went off in Damon's head.

"I would like to make a wager," he started.

"What would you like to bet on, Damon? How much you can annoy me?"

He smiled at her. "Today is December 1st. I think that I can make you like Christmas by the 25th."

"What's the prize?" She asked him.

"If I win, you have to spend Christmas with me." He said.

"And if I win?"

"Then, I'll decide that you're right-that Christmas is a waste of time. And I won't celebrate it this year." He said.

"Hmm..that's a big loss on your end. You must be pretty confident that you can convert me."

"I am. So, what do you say, Elena?" Damon asked her, extending out his hand to her.

She looked him in the eye for a few seconds before sighing. "Deal." She said while shaking his hand.

"Just you wait, Elena. You're going to be one of those people who decorate their entire yard with Christmas inflatables by the time I'm done with you."

"God, no."

Damon just smiled at her. He was looking forward to his next twenty five days with Elena.