A/N: This takes place in the second season after Katharine told Damon she didn't love him, and Stefan and Elena are broken up, which is stated again in the chapter. This only matches up with the outside world of the show somewhat, but it's not important for this story. It is very much fluff. This first chapter is very heavy on summary, but things needed to be explained. The following chapters will be much more scene-driven. Please read and review!

25 hours

Elena knew it was a stupid idea to challenge a vampire to anything, well, maybe anything besides who can stay out in the sun the longest without jewelry, which taken out of context was silly and in context was impossible, on the vampire side at least. But other than ring-less tanning, Elena was sanely aware that vampires had the upper hand on pretty much everything else…unless there was some vervain eating contest. That didn't sound too appealing, but she'd win.

She scraped her nails across her scalp. Softly tugging a clump of her hair, she tried to almost physically pull out another headache coming on that she wasn't sure was from the Red Bull caffeine-crash or not sleeping for twenty-five hours. Because Elena Gilbert, former level-headed high school junior, was then Elena, the girl who bet her vampire ex-boyfriend's vampire brother she could stay awake longer than he could. And this decision was made knowing he was undead and nocturnal and well, Damon. But, Bonnie had magically sealed her in the house for the duration of the first three weeks of summer break because there was some new vampire drama going on she was being kept in the dark about, and Bonnie didn't want Elena doing anything irrational after her breakup with Stefan, which was for real this time. There was supposed to be some round-the-clock Elena-watch bull crap, but people were busy with the aforementioned vampire drama and Jenna was in the Outer Banks of North Carolina with Alaric, which left Damon sitting on her windowsill with a duffel bag and a smile that could have had all the bikinis in a three block radius dropping on the spot.

At first she was sullen, because sullen or distant or pouty was an option when she'd only been missing the outside of her house for half a day. He had rolled his eyes when she wouldn't talk to him. And she kept her eyes on her diary, doodling in the margins until he sped out in that whoosh-less Superman way he always did. It kind of had her thinking of Damon in blue tights, and maybe kind of not hating the image.

Two days later she was a little lonely. After four days she'd run out of frozen pizza. On the sixth day she'd succumbed to How I Met Your Mother reruns, and she wished she had that compulsion thing to make Damon come back. But she didn't need to be a vampire to have him knocking, yes knocking, on her front door. This time he was carrying a plastic bag of Wendy's, and she let him inside with a neutral expression. Ten minutes later she was laughing, and she tried to convince herself she was only having such a good time because she was people-starved. They ate standing up in the kitchen because her butt didn't want to be one with the couch anymore, and they were still in there long after the last French fry and the keep-away game with a ketchup packet. At around midnight Damon said it was Elena's bedtime, mockingly calling her a little girl or something, and she could remember crossing her arms over her tank top, eyes narrowing, and him raising his eyebrows like she'd already made the bet.

When she did make the bet, he didn't seem very interested, reminding her that he was like, you know, a vampire. But she reminded him that he still slept, she'd seen him sleepy and cranky before. She also may have made the game a little more intriguing when she mentioned the only way to make sure neither of them fell asleep was for Damon to be there 24/7, and she may have tightened her crossed arms closer to her chest, leaning forward on the counter, because cleavage-leverage seemed fair when she was facing weeks of summer vacation inside.

He agreed, asking her the prize/punishment for the winner and the loser. She told him she really hadn't thought that far ahead, and he accused her of bluffing, walking past the dishwasher like he was leaving. Her brain was scrambling for something, anything, and she blurted out something along the lines that if she won, he had to wear a Superman costume. He turned at the armrest of the couch, calling it kinky, coming up with his response much quicker, saying if he won, he wanted to see her naked. She called him a perv. He thought it over for a second, shrugged, and nodded. Then he said if it was too much of a risk, because after all, he was going to win, that she should just call it off. There was something that snapped inside of her and she shook his hand, telling him it would start the next day at nine o'clock.

Damon was there five minutes early, carrying a large supply of blood bags, some groceries, and his duffel bag from before. Elena went about her day as usual with Damon making phone calls to Bonnie, Stephan, and Caroline to tell them he was going to be busy for a while. That night they spent the time talking, making fun of Stephan, and listening to loud music. At nine am the next day, Elena had a Red Bull. She had another an hour later. It was ten in the morning, twenty-five hours in, and she was ashamed she was already Red Bull-dependent, and she had a killer headache.

She let the hair clasped in her hand fall back down, and opened the freezer for a few ice cubes. Wanting to wake up, she pressed the ice to her forehead, over her eyelids, and across her neck and collarbone. Just as her fingers were going numb she saw Damon leaning against the sink.

"You should tell me when you do that again," he said.

She wasn't sure if it was the pain under her skull, but she walked up to him, and flicked the excess water in his face, smirking when he looked upset.

The he smiled. "I see you get more mature when you're sleepy." When Elena didn't respond, he splayed out his hand to show two blue pills on his palm. "I heard you muttering something about a headache." He opened her fist and tilted them in her hand before walking away.

"Thanks, Damon," she said. She was surprised he would do something so considerate, until she studied the pills and saw two tiny letters on each tablet: PM. "Tylenol PM? Damon!"

He was back at her elbow. "What? I would have waited for you to wake up to see you naked."

"Damon!" He was gone before she could say anything else, and she dropped the pills into the trash. "This week is going to suck," she whispered to herself.

"Like you'll last a week," Damon yelled from another room in the house.

Yep, this week was definitely going to suck.

A/N: Again, please review! This is my first Vampire Diaries fanfic.