Disclaimer: I do not own The Vampire Diaries TV show. That honor goes to Julie Plec and Kevin Williamson.

Hello, my lovely readers. I came up with this truly crazy idea for the first annual Klaroline shipper games because writing new one-shots every week was becoming tiresome when I still have a month of school before the summer break. In the meantime so that fans know that I have not given up hope I had this crazy idea… and here it is. On with the show…

Chapter 1: Boredom Breeds New Games

Laying on one of the couches in the Great Room of the boarding house, Damon Salvatore contemplated his ceiling. He was so very, very, VERY bored. There was nothing exciting going on right now. Elena and he had called it quits. Yet again. Enzo was… Honestly, Damon had no idea where Enzo was off to. Witchy was off playing with either Little Gilbert or Witchy Junior with the attitude problem. Then there was Stefan. Who the hell knew what his baby bro was up to?

Rolling his eyes, Damon downed his bourbon and got up to walk over to the side table for a refill. Glaring at his fireplace it occurred to Damon that he had forgotten about Caroline. "Maybe she's off mating with Papa Hybrid in my woods again?" Damon mused to himself and he rolled his eyes. Nah. Caroline was probably sitting around a local church asking for forgiveness for her sin of letting herself do anything that might be even mildly interesting. The baby vampire needed to loosen up a little…

Tapping his foot against the carpet, Damon thought more deeply about the idea of what could cause Caroline to loosen up a little. 'Alcohol? Yeah, but Caroline already drinks a lot. Not one for the responsibility books this week. Nope.' Staring into the fire, his mind continued to drift until it hit him. "Of course," Damon said with a chuckle.

"Of course what, brother?" Stefan called, walking into the room with his typical brooding look.

"Klaus," Damon said happily with a wide grin. "Klaus is the answer."

Stefan's eyebrows rose and his lips formed a thin line. "Klaus is the answer to what? And why do I have a bad feeling about this?"

"Klaus is the answer to our Caroline problem," Damon announced excitedly.

"What are you talking about? Did you mix Prozac with your bourbon again? Because you remember how long we had to lock you downstairs in the cell the last time after that happened?" Stefan folded his arms over his chest and frowned deeply.

"I am not on Prozac. Nor would I ever willingly ingest any kind of anti-depressant. Those things have severe side effects. That was another one of Little Gilbert's and the Football Player known as the Least Valuable Part of the Team's idea," Damon snapped with a glare. Deciding to ignore his brother momentarily, he pulled out his phone and began to type texts to everyone he knew that he thought should be included in this.

"What are you doing?" Stefan questioned Damon, not really wanting to know but feeling worried for his friend. If Damon was up to something that involved Caroline then, as a good friend, Stefan should at least try to stop his brother.

"When was the last time anything interesting happened around here that did not involve one of us being maimed of nearly killed? Or in a few cases actually killed," Damon replied while continuing to text.

"It's been awhile. But what does that have to do with Caroline… and Klaus?" Stefan responded slowly, coming to sit down on the couch and sitting sideways to look up at his brother.

Pocketing his phone, Damon walked around to sit down on the table in front of his brother. "It has everything to do with Caroline and Klaus. Do you know that the only time that Caroline has shown any sign that she cannot be so… uptight was after her little thing with Klaus?"

"Yes," Stefan nodded and sat back. "And?"

"And I think that we should start a game based on trying to get those two crazy kids together. Think of it. We'll have an unlimited supply of Klaus's blood for whenever Tyler or an out-of-town werewolf decides to take a bite out one of us. Caroline will be less bitchy. Tyler will go nuts. I mean what's not to love?" Damon slapped on his knees when the doorbell rang. "And that, my brother, would be the first arrival of one of our contestants."

"Damon, what's going on?" Elena asked, looking worriedly up at Damon. "Did someone get hurt? Did you see Jeremey with another witch girl again?"

"No. And no. Everything is cool," Damon replied with a lazy grin.

Sighing in relief, Elena brushed her hair behind her ear. "O-kay. So, why did your text saying that it was urgent?"

"Because it is," Damon called over his shoulder as he headed back toward the Great Room.

Elena stopped when she saw Stefan. "Hey. Do you know what's going on?" she asked, tucking her hair behind her ear again.

"You'll have to ask Damon. It's his idea," Stefan replied with a shrug before getting up to pour himself a drink.

The doorbell rang again and Damon walked out of the room to collect the next guest. "Hello, Jeremy," Damon called loudly enough to cause Elena to come out to stare at her brother in confusion.

"What do you want, Damon?" Jeremy asked, crossing his arms.

Damon smiled before yanking the young hunter into the entryway and slamming the door behind him. "I want you to get your smart ass into the Great Room and sit the hell down."

"You're not my dad," Jeremy snapped, brushing Damon's hand off his shoulder.

"And for that I profess gratitude to the universe every day," Damon retorted as the Gilbert siblings settled on the couch across from Stefan. "Now that you are gathered here, it's time to explain the rules of the game -" just as he was about to begin listing off the rules, his phone beeped. His eyebrows rose as he opened the text. "Or not. You know I think that we have to wait for another hour before we can truly start this game."

"Good, because I have things to do," Jeremy stated as he pushed himself to his feet.

Damon sped forward and pushed Jeremy back down. "Oh no, you don't. Your sister and I have enough to worry about wondering which witch you're spending quality time with and whether you're trying to get yourself killed is not a top priority that I want to indulge in at the moment."

"We can't just keep him here. We need to trust him, Damon," Elena protested.

Rolling his eyes, Damon stared Elena in the eye. "As much as I would love to try doing that right now I would like it if you would humor me. If you decide to opt out of the game after I explain it later tonight, then you know where the door is, Lena."

Elena looked at Jeremy, biting her lip and Jeremy huffed, falling back against the couch cushions. "Can I at least have a beer?" Jeremy asked and looked up at Damon who looked at Elena. She sighed and waved a hand.

"I'll take a bourbon," Elena muttered while Stefan got up to pour it for her.

Damon strolled into the kitchen and grabbed a beer for Jeremy and then walked back into the Great Room. He was shocked to see that everyone was still there. He had expected them to get up and leave. "What is this about, Damon?" Elena asked him as if repeating the question would get a different answer. He waved a finger at her.

"Not until the other contestant arrives," Damon told her and handed Jeremy his beer.

"So, this is some kind of game?" Jeremy looked at Damon for confirmation.

"And to think that this kid does not have all As in his classes," Damon shook his head with a chuckle.

"What kind of game is it?" Elena asked and Stefan opened his mouth to answer when Damon held up a hand.

"No, not till everyone is here. Does everyone in this room need a hearing aid?" Damon rolled his eyes.

Several hours later, Damon had to field the same questions over and over again. It was becoming enough to make him want to stake himself. But that was nothing new. When the doorbell rang, he jumped to his feet and sped to the door. Yanking it open, he smiled with joy that he never thought he would feel seeing the vampire in front of him. "Rebekah," he murmured.

Narrowing her eyes, Rebekah walked past him. "Matt?" Whirling around, Rebekah glared at Damon. "Where is he? What did you do to him?"

"Nothing. Matt's fine. As far as I know. Haven't seen him today," Damon told her.

"Rebekah?" Stefan called, looking confused as he came to stand in the entryway.

"Yes, Stefan. The Original sister is our last contestant. Now, if you will follow me, then we can begin," Damon waved them forward.

"I cannot believe you, Salvatore. I ought to rip your internal organs out and feed them to you," Rebekah was saying as she came to stand in the Great Room.

"Rebekah?" Elena whispered, looking shocked.

"Elena," Rebekah replied drily, keeping her attention focused on Damon. "I suppose I should apologize, since I am about to kill your boyfriend, but I don't feel like it."

"We're not together anymore," Elena mumbled, staring at her glass of bourbon.

"Pity. I thought you were a nice fit, since I don't like either of you," Rebekah told them. "Now, where was I? Oh, yes, killing you," she informed Damon, reaching for his throat.

"Oh, whoa there," Damon held up his hands. "Okay. Yes, I lied to get you here. But it was important. You see, things have been really dull around here," Damon noticed that his fellow Mystic Fallers were about to protest. "Well, there have been a few incidents but nothing that has been enjoyable. So, I thought that we could start a game."

"You had me convinced that Matt was dying so that you could get me to come all the way here for a bloody game?" Rebekah growled and then relaxed. "I suppose that makes sense in your twisted, little brain."

"Yeah, it did. Anyway, I was bored and then I came up with this idea of a game involving trying to get your brother and our resident uptight, baby vampire together."

"You want Elijah and Elena to be a couple?" Rebekah replied, looking from Damon to Elena.

"NO!" Damon shook his head vehemently. "Klaus," he started to say when Elena paled.

"You want me to be with Klaus?" Elena whispered, her voice barely audible.

"No, he wants Klaus to be with Caroline," Stefan explained quickly.

"Oh, thank God," Elena sighed in relief.

"What does that have to do with us?" Jeremy asked.

"It's a game," Damon told the younger Gilbert. "Each of us will find a way to try to get Klaus and Caroline together and whoever is the most successful in their efforts will be crowned the biggest Klaroline shipper."

"Why? What? How? Are you out of you mind?" Damon's friends echoed and he sank down onto the couch beside his brother. It looked like it was going to be a very long night while he tried to explain how they could all benefit from this game. Hopefully, they would not all walk out on him before the night was over and the game could begin.

Okay. I really hope you liked the beginning of this story because I have no idea where it is going from here but there will be a new chapter next week. I will be including characters from TO who I think would be likely Klaroline shippers like Hayley, Elijah, Marcel and possibly others. There will probably be some moments in which characters like Katherine, Silas and Kol add their opinions. You will see my reasoning of why the TO characters would make good Klaroline shippers in either chapter two or three. If you have a theory about who would make a good Klaroline shipper and why on either cast, feel free to let me know in the review.

As always thanks for reading, faving, following and reviewing.

Peace,

LL