AN: So, this is my first real crossover I've written and I gotta admit, it started out as pure crack. I just love both the Vampire Diaries and Vampire Academy and I thought, wouldn't it be funny if the characters interacted. And so this little thing was born.

Ok, so here are some basics, in case it isn't clear from the the text. This all takes place in the Vampire Academy world, after the last book, but before Bloodlines. (So some spoilers should be expected, but nothing from Bloodlines) The Mikaelson family are normal Moroi (or are they? dumdumdum) and that is all you should know for now.

This is going to be a series and we will totally see more characters from both works interact, but Adrian and Kol are the centerpieces. I hope you'll have as much fun reading this as I did writing.

Warnings: Some talk of depression and some light violence.

Chapter 1. Going Down.

The drumming beats of the music and the mindless chatter of the girl who was currently draped over his arm were doing nothing but bad things for his headache. Adrian downed his drink, knowing full well that it would only make the next morning an even bigger hell then usual, but he had come to the point were he had stopped caring.

This was the fourth night in a row that he was holed up in some sleazy club, after escaping from Court, drinking his sorrows away. That was a herculean task, even for a self proclaimed alcoholic like him.

His mother was facing jail time, his father was worse then ever and Rose ...

A jolt of pain went through him and for a moment darkness seemed to cloud his vision.

And the girl just went on jabbering, her voice thankfully mostly drowned out by the relentless beat of the music. What was her name again? Adrian tried to remember, tried anything to stop his mind from wandering towards Her.

Rose.

She was what started this all, this four day binge.

After the events at Court he had hidden himself away, not ready to deal with prying eyes and disdainful looks. He had longed for a drink then, practically went down on his knees and prayed for a bottle of vodka to appear in his parental home. But he had stayed painfully sober while his father ran around talking with lawyers and barking orders at him about keeping up appearance.

He had actually been secretly proud of that, of staying sober when all of that was happening. It made him feel almost in control.

But all of that had changed.

Because of the most stupid, pathetic reason. Because he was insane. Because he couldn't handle seeing Her, seeing Them.

They had been standing across one of the many little courtyards, holding hands, just talking to each other. Rose and Dimitri, Dimitri and Rose. The golden couple. The happy heroes.

And for a moment there Dimitri had looked up and their eyes had met.

Of all the emotions he could have showed, all the looks he could have given Adrian with his stupud face, like surprise, or guilt or even that stoic Guardian stare he was so good at, it had to be pity.

Pity.

His control went out of the window in the first bar he found.

"Dex." The girl beside him whined and it took him a moment to snap out of it and remember that that was the fake name he had given her.

He looked at her, with her fake red hair, big dumb eyes and just awful attitude and he felt like throwing up. Probably wasn't her fault, so much as it was the four shots of tequila, two whiskeys and whatever the hell there was in a Slippery Nipple.

"I'm thirsty, Dex." She went on, pouting as if she was a toddler.

What on earth was he doing with her, she was nothing like ...

He jerked violently away from her , as if that would stop the thought from forming in his head. The girl, he really could not remember her name, looked at him as if he had just grown another head.

"Buy your own drink." He sneered at her, then quickly took off towards the exit, before he had to deal with her reaction.

The club was crowded, so he had to weave through groups of dancing girls and drunk suits. His head was throbbing and he couldn't help but ask himself what the hell he was doing. Leaving Court, running off to a city without any Guardians, getting wasted every night.

He was at the front of the club now, near the booths where couples were making out, somewhat hidden from the prying eyes of the rest of the club.

He had wanted to get away from it all, from Court and from his own head. But there was no escaping the spirit madness, he could feel it now, coiling around him like a snake, choking the life out of him.

"Ivashkov!" A voice called out from amongst the noise and for a moment Adrian stood stunned. Whoever it was, whoever had found him here, he didn't, couldn't, deal with them now.

Then a hand clasped on his shoulder and a face doomed up in front of him.

Short dark hair, even darker eyes that nonetheless seemed to shine playfully in the darkness. Strong features girls used to go crazy over and of course that mouth that was simply made for smirks and grins.

"Mikaelson." The name escaped his lips without his brain getting in the way.

Kol Mikaelson smirked, of course he did, and those lights in his eyes seemed to brighten.

"God, it's good to see you." Kol said in that English drawl of his, before his eyes traveled along his face and body. "Though, I have to say, Ivashkov, you look like shit."

Again it seemed like a witty reply just came out of his mouth on its own accord. "We can't all be as obsessed with our appearance as you are, Mikaelson, how many hours did you spend in front of the mirror today?"

"See, I've missed that charm of yours." Kol shot back, amused. "Come, have a drink with me."

Part of Adrian longed to tell him no, to go back to his hotel room and go to bed. It wasn't like he and Kol had ever been good friends. They barely counted as acquaintances to be exact. But there was something about him and their moment of banter that reminded Adrian of the good times in college, when the world was a much easier place.

So he ignored the dark feelings that were playing around in his head and sat down in the booth with him.

"One drink." Adrian warned though, feeling that he had already reached his limit.

Kol rolled his eyes at that. "When have we ever stuck to that?"