Chapter 1 - Matchmaker - Edited 1/23/14

About the story - This will be my longest fic (about 20 chapters plus). It will cover Klaroline's relationship over a period of 10 years. I have this story laid out from beginning to end BUT I am totally flexible in incorporating special requests of things that you want to see happen and I am already working on the next chapter. I will be following the update schedule that is at the bottom.

Happy Reading

Stefan POV- Waltham, MA - 2013

She is NOT going to beat me again. She is not going to win! This time...This time I'm going to be the trash talker! The thought makes me laugh manically in my head, the thrill of actually winning surging through me.

I glance up at Caroline. She is holding her cue stick casually, her face void of emotion except her lips keep twitching, obviously itching to turn into a smirk as she watches me take the shot. The lone 8 ball is in the middle of the table and it's a race to see who can hit it in first.

This is our 9th game today, but our Pool Battle Diaries started 2 months ago, about 1 month after we met at the Second Chance orientation.

Dear Caroline just came into the Second Chance Program straight from high school and I, as an alumni of the program, was serving as a mentor when we met at the event and hit it off. Once we started talking, I found myself so happy to get such a cool mentee. At first, I admit, she looked like the stereotypical, brainless blond caring only about her hair, makeup, clothes and nails.

Shallow.

Boring.

Yet, when we started talking, I quickly found out she was anything but those things.

Don't get me wrong, she DID care about all that stuff and was even Miss Mystic Falls (which, by the way, is the same hometown I'm from) but she had things rough too. She freely shared with me her story of coming to Mystic Falls from Australia when she was 13 because she was diagnosed with cancer. Mystic Falls, since it is well known for being at the cutting edge of cancer treatment along with Boston, is not a shock as to why she ended up there. Her father, who, luckily was in Mystic Falls at the time working to bring the rest of his family to the States, pulled some strings and got them here so Care can get help.

Care is one of the lucky ones where her treatment worked and she has been cancer free ever since. She eventually got to enjoy her high school years, becoming a cheerleader and participating in every school event under the sun but her grades suffered due to attendance, so much so that no college would accept her.

It wasn't until she heard about the Second Chance Program that Care got her second chance, like we all did.

The Second Chance Program was her ticket into higher ED like it was for Damon and I and so many others. Second Chance was really our final chance for those of us who screwed up high school (ie. Damon and I) or just didn't have the grades (ie. Caroline) to prove our case, to convince our prospective professors and leaders of the program, like Alaric and Meredith, why we are college material despite our records.

And we had one year. One year to get no lower than a B- in grueling remedial courses on top of four university courses of our choice.

It was an academic boot camp that produced such discipline through sweat and tears that you were never the same once you got out.

Never mind you were forever bonded with those who went through SC like you did.

Once you were out, you could decide to stay in dear old Fall River where SC was based, or spread your wings and fly away like my best friend Kl...

"Are you going to shoot sometime this century Stefan?"

I look up at Care whose stoic expression is gone and is replaced with an amused one.

"We all know you are going to lose. Isn't that right guys?" she says cockily, the small crowd surrounding our table laughing loudly in response.

I narrow my eyes at her irritably. "Whatever Caroline," I grumble.

"She does beat you every week you two come into the gameroom," chimes in Jeremy, evoking a new wave of laughter.

I bolt up from my shooting position, officially pissed.

"Aren't you supposed to be working or something, gameroom supervisor?!" I snap viciously.

He rolls his eyes at me. "Maybe if your suckiness wasn't so bad that you drew a crowd, I wouldn't have to come over here to find out what was going on, dick!"

Before I can say anything, Care clears her throat loudly. When she gets my attention, she gestures towards the pool table. "Any day now. I do have to study for Alaric's test tomorrow."

I grimace at that, emphatic to her situation, immediately focusing on my shot. Alaric's tests are brutal.

I take a breath, looking at the 8 ball. All I need to do is cut the ball. This shouldn't be hard.

"8 ball..."I say, using the cue to hit the right corner pocket. "Corner pocket."

I move the stick up and down, aligning my shot with the cue ball.

"I smell a scratch..." she says in a sing song voice.

I can't help but chuckle at that. "Shut up."

Finally, I take the shot, just when Care lets out a loud, exaggerated cough, startling me.

"Care!" I shout at her in mixture of anger and despair. She just giggles at me, like her cheating is funny.

The whole room watches the cue ball hit the 8 ball that goes sailing into the right corner pocket. The cue ball starts moving with dangerous speed towards the left corner pocket and I just want to cry.

I cringe, closing one eye as the cue ball hovers over the hole.

When it falls in, Care shouts happily, raising her hands up in the air like Rocky on the freaking steps.

I groan as she starts the "Care victory dance", the crowd egging her on as they chant her name:

"CA-RO-LINE! WHAT! CA-RO-LINE!"

When Jeremy decides to be Caroline's dance partner and they start moonwalking, I'm done. Seriously? Can someone please shoot me?

I must of looked really dejected, because Caroline takes one glance at me and stops, the crowd groaning in disappointment. They quickly disperse, Jeremy moving them away from the table as Caroline comes and gives me a big hug.

"Did you really have to start moonwalking?" I grumble, hugging her back eventually.

She pulls away a bit, looking embarrassed and apologetic. "I might of gotten carried away."

"Yeah, maybe," I say sarcastically.

She gives me a nudge. "Don't be a sore loser."

"You cheated!"

Her mouth drops in mock offense. "Me? No..."

"You coughed just when I was going to take the shot!"

"I couldn't hold it!"

"That cough was so fake! It's as fake as Bonnie's weave!"

Caroline laughs loudly. "Oh no you did not just make fun of her hair?!"

I laugh back, putting our cue sticks away.

"Me? No..." I say, mimicking her earlier response.

She laughs. "Wanna grab some food from Saltzman Cafe?" It's weird that they dedicated a building on Campus to Alaric but honestly, he's done so much for this university, it isn't shocking at all. He'll probably be President soon. "It should be open right now..."

"I can't, remember? Alaric? Test?" says Caroline, grabbing her book bag.

"Let me walk you back to your dorm then," I offer quickly. She throws one of her winning smiles and nods enthusiastically.

Once we cross the street to where the freshman dorm rooms are, she breaks our comfortable silence.

"I so can't wait for Winter Break," she says longingly. "Finals are killer." She turns to me. "Was it this hard for you when you were in SC?"

"Yeah, Kid. You're not special," I tease. "Speaking of break, you got any plans?"

She shrugs before she readjusts her bookbag. "Not really. Just going home."

"Ah. Good old Mystic Falls."

"Are you ever going to go back Stefan?" she asks softly.

"I don't get the point. My parents are dead. There really isn't anything left there. Since Damon sold the house and moved to Boston, I think I would go there more than anything. Probably while I'm over there I can catch up with my best friend..."

Then a light bulb goes off in mind, making a sinister grin spread on my face.

"Oh no..." groans Care. "I know that look. You've thought of something and I don't think I'll like it..."

But I will. God! Why didn't this come to me before?! I think, getting all excited.

Because you thought you could miraculously beat her in pool sometime before you died, says a another mental voice with a snicker.

Shut up brain! It was a rhetorical question! Now...I mentally rub my hands eagerly together. Back to my vengeance plan. Sure, I can't take Care out in pool, but I know who can...

"Want to go to Cambridge tomorrow night?" I ask suddenly.

Caroline arches her eyebrow at me suspiciously. "Why?" she asks slowly.

"Well. I have a friend of mine I want you to meet. You too are so alike, come to think of it. His name is Klaus and..."

Caroline interrupts me with a loud groan. "Oh hell no Stefan! First Damon, now this guy? I thought you were over this whole matchmaker thing!"

I pause, momentarily confused because that was SO not I was doing, but...

My mind automatically melds this new idea with my master plan of revenge, deciding this matchmaker business is the perfect cover up. So I go along with it.

"Caroline. You've been single forever! As your mentor, I'm giving you advice: Get. A. Man! I know Elena agrees with me."

"She always agrees with you," she whines. "She's your girl first and my roommate second."

"Seriously though. Klaus is a great guy!"

"Really," says Caroline flatly.

"Yeah! Like us, he did SC..."

"Great. A high school delinquent like you and Damon. Just what I need," she interjects sarcastically.

I ignore her. "He's at Harvard now," I say slyly, knowing that would take her for a loop.

Her eyes bug out. "Oh Alaric must looooooove him! SC to Harvard? He might as well be the program poster child!"

"Oh, he was. Four years back."

She gapes at me for a moment, then mumbles: "Nerd."

"You're the last to talk, Miss straight A's in all her classes, which..." I smirk at her when I realize another thing they have in common, "...hasn't been done in the history of SC since Klaus."

She shakes her head. "Now you're making stuff up."

"I'm not. Ask Alaric and Meredith tomorrow. They'll tell you."

Caroline takes her keys out to open the door to her dorm room.

"Anyway. What do you say? Thursday?" I ask hopefully. Finals will be over then and Klaus could so crucify her! I swear that guy can beat people at pool in his sleep.

"I'll...I'll let you know." No she won't. "Bye Stefan!" she adds hurriedly, running inside.

I smile, turning around as I pull out my phone.

"What?" answers a British, male voice laden with sleep.

"Klaus."

I hear him clear his throat. "Oh. Hello mate. What..." he yawns loudly. "To what do I owe the pleasure?"

I shake my head. "What the hell are you doing sleeping at 7pm?"

"Sod off Stefan," he huffs grumpily. "I was studying and my bloody brain went on standby."

I laugh. "That's all you do. Study. You need a girl." As I say that, I think of Caroline and the conversation we just had, the irony not escaping me. "And I have a prime candidate. Smart, funny, beautiful..."

"Know what?" says Klaus irritably and suddenly more awake now. "Why don't you go on Love Connection and murder the host so you can have his damn job? Don't you ever tire of playing matchmaker? Remember Tatia? What a monumental waste of my existence thatwas."

"You know. Your future wife said something similar after she beat my butt in pool...again," I frown at the end, the loss still a sore subject.

A good 30 seconds goes by and I almost think we got disconnected before he says a matter-of-factly:

"She plays pool.

Got um...and funny he didn't refute the future wife comment...

"Yeah," I say, still pondering that last thought.

"And she's good?"

"She's actually the top player in our game room in Saltzman."

"Oh really?" and I can hear his level of interest growing.

"Uh-Huh."

"Well. My interest is piqued." Well. No shit Sherlock. But I don't say that and instead decide to go in for the kill.

"She's probably better than you."

He lets out a loud, raucous laugh, obviously offended and I knew my mission was accomplished. "Not bloody likely!" he finally says. "Tell you what Stefan. I'll be done with finals on Thursday..."

Oh, how CONVENIENT! The stars have ALIGNED! I barely refrain from doing a happy dance.

"...and I'll go down to good Old Fall River to set the record straight," continues Klaus on his tirade. "Make sure you're there to give your lady friend a shoulder to cry on when she loses! Good night!"

Click.

I smile in satisfaction at the phone, not even mad he hung up on me. I dial another number as I get to my dorm room, intending on giving the prime target of my vengeance another go with a different approach.

Let's see how alike they really are...

Caroline picks up. "Stefan, I really need to study..."

I go straight for the jugular. "My friend Klaus says he can kick your ass in pool and that you'll need my shoulder to cry on once he's done with you."

A pause. Then: "What did that asshole say?!"

Yes. I'm so evil...

A/N Next time - The Pool Battle Diaries continues guest starring Klaus.

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