A/N: This story idea came from itsCaroline, who has very kindly let me run with it. It's quite a bit different from anything else I've written, and I was a little unsure about the AU/AH aspect, but I'm really excited about it. So, please let me know what you think. Please review. And I'll try to post as fast as possible.

Disclaimer: I do not own The Vampire Diaries.

Bonnie Bennett was sipping coffee in her kitchen, waiting to see if her roommate, Elena Gilbert, would surface. The poor girl had been sick with the flu for the past three days, only leaving her bedroom to use the toilet, for whatever reason was most urgent. To Bonnie's surprise, Elena rushed into the kitchen, a blur of long brown hair and clicking heels.

"Feeling better?" the dark-skinned woman asked.

"Mm," Elena mumbled through a mouthful of toast. "Much. And I'm starving."

"You should be. You've been throwing up non-stop for the past three days. There's nothing left in there!" Bonnie poked the other woman's stomach and then leaned back in her chair, sliding the A section of the New York Times across the table for her roommate to read. "Looks like they've soldiered on without you at the paper though."

As per usual, now that Elena was immersed in the days news, no answer was forthcoming. She was a reporter, a journalist for the New York Times, and highly celebrated in her field. At twenty four, she was the youngest writer on staff for the respected publication, and never disappointed in her candid and exceptionally well-researched pieces on the legal problems facing the Big Apple.

Given the reporter's intense absorption of just about any newspaper she could get her hands on, Bonnie was surprised when a hiss of displeasure sounded from across the table, and paper was slammed down.

"This man is disgusting!" Elena exclaimed, pushing the offending item away.

"I dunno," Bonnie replied teasingly, looking at the picture on the front page, "I think he's gorgeous."

The other woman moaned and tugged the newspaper back. "Well, yes, I have eyes, thank you. I was talking about his harem, his cute little group of girlfriends. It's disgusting, and sexist, and -"

She stopped suddenly, choking on her own indignation.

"Well then, you aren't going to like what I have to tell you."

Elena's head snapped up and she eyed her roommate suspiciously, remaining silent until Bonnie spoke again in a mocking tone.

"One of your colleagues dropped by yesterday. Apparently, in your absence, you've been assigned to attend the upcoming charity ball at the Salvatore penthouse. You're writing a story about how wonderful his work is, and yes, how and why he has four live-in girlfriends. Since he's a lawyer, they've given it to you. Slow news week I guess..."

Bonnie watched as Elena remained silent, her mouth open a little, appearing to wait for the other woman to take it back, say it was all a joke. Bonnie cracked a half-smile. It wasn't a joke. And when Elena seemed to realize it, she turned a dark shade of red.

"Sonofa-"

"I hate these things," Damon Salvatore grumbled, glaring at his own reflection in the full-length mirror in his bedroom, trying (and failing) to adjust his black tie properly.

Rose walked up to him, her golden beaded dress making a soothing sound as it dragged along the floor, and slapped his hand away, stepping between him and the mirror and smirking at him. He always complained about the various social events that he attended, and she always teased him mercilessly about it.

"Maybe you should consider retiring from public life then. You could live alone, in a shack, in the middle of nowhere," she responded flippantly, laughter reflected in her green eyes.

"And how would I survive without you?" he quipped.

Before she could respond, a chipper voice sounded from the doorway.

"Is he still in a pissy mood?" a young blonde woman in a skin tight, bright blue dress asked.

Rose looked over Damon's shoulder to see her house-mate Caroline leaning against the doorframe, Jessica standing right behind her, the straps of her light-pink gown visible around her companion, her eyes wide and nervous, as usual.

"I am not pissy," Damon snapped, turning on his heel to glare at girlfriend's-number-three-and-four, as Andie, girlfriend-number-two strode in, sparkly floor-length dress flowing, clutching a necklace. "It's her fault!" he exclaimed, pointing at the statuesque woman, who cocked an eyebrow in response.

"I am not the master of your moods, Damon." She looked at Rose. "Can I borrow this for tonight? The clasp snapped on my gold chain, and I don't have anything else that matches."

Rose nodded as Damon spun back to pout pointlessly at his reflection.

"If you weren't leaving..." he drifted off.

Andie simply rolled her eyes and scoffed, winking at Caroline and Jessica before leaving the room.

"People are gonna start showing up soon," the blonde pointed out. "Jess and I are gonna go wait downstairs if you're gonna keep having a tantrum up here."

"I am not having a tantrum!" the blue-eyed man blurted, causing Caroline to snicker and Jessica to squeak nervously.

Without another word, the pair left, leaving Damon and Rose alone again.

"You know," the woman began gently, cupping her boyfriend's face and forcing him to look at her, "You could solve this whole thing by just settling down again. You're thirty now; get married, start a family."

He smiled affectionately, and place his hands on her hips.

"Would you marry me?"

Rose laughed and stepped back. "I told you last time, sweetheart, I will never marry you."

"Well then," he stepped back to pull on his black suit jacket, and then offered her his arm. "I guess I'm stuck, because no one else would ever put up with me."

Elena smoothed out her black, floor-length dress nervously as the cab brought her closer and closer to Damon Salvatore's penthouse. She wasn't too sure why she was so anxious, beyond her disdain for the man himself.

She had done her research; she knew that he was a lawyer, had inherited, with his best friend Alaric, the law firm 'Salvatore & Saltzman', that he had studied psychology before going to law school. He did a great deal of charity work, had been married and divorced about five years before, and now tended to surround himself with an average of four girlfriends at a time.

His current girlfriend's, in chronological order, were Rose Ingles, a teacher, Andie Starr, a television news anchor, Jessica O'Reilly, unemployed, and Caroline Forbes, a Broadway actress.

The rest of Damon's life seemed very impressive, until one got to the part about him very clearly taking advantage of and objectifying women. It was disgusting, and patriarchal, and misogynistic, and Elena had decided that she didn't like it one bit.

Too bad her job required her to be unbiased.

So when the car pulled up at her destination, she pasted on a practised smile, and slid out of the car, her media credentials in hand. When she had been cleared through security, she made her way up the elevator into the massive foyer where most of the guests seemed to be congregated.

There were lit candles everywhere to add to the dim lighting from the high ceiling. The white room opened into a large staircase, presumably leading to the more private area of the home. People were wandering, commenting on works of art and the depth of library, and how wonderfully brilliant and generous Damon Salvatore was.

This, she could manage without a problem. She plucked a flute of champagne from a server walking past her and glided through the crowd, scanning the faces for anyone she recognized. There were a few familiar people for her to speak with. Finally, one of her acquaintances pointed toward a bubbly blonde woman cutting through the crowd.

"That's Caroline Forbes," the acquaintance whispered, "She's one of the girlfriend's."

Elena nodded and excused herself, making a beeline for Ms. Forbes. She tapped the other woman on the shoulder, and smiled when their eyes met.

"Hi," she extended her hand, "I'm Elena Gilbert; I'm with the New York Times."

"Oh!" the blonde's smile widened, and they shook hands, "I'm Caroline. It's nice to meet you."

"Likewise." Elena's spoke through the grin plastered to her face. "I'm just wondering if you have time to talk to me for a few minutes? Just to answer a few questions?"

The other woman's face brightened and she nodded enthusiastically.

"I'll be happy to answer whatever questions you have, but when Jessica gets back, I'll probably have to go."

"Oh?" Elena mumbled, reaching into her purse to pull out her recorder, "Why is that?"

She clicked the device on, and Caroline's eyes jumped from it, back up to Elena.

"Well, Jessica's a really sweet girl, but she has a hard time. She's got a really bad anxiety disorder, and usually doesn't leave home. Damon gets her to come out for these kinds of things, but they really freak her out. Talking to a reporter, being in the news, probably not good for her."

"So Damon forces her to participate in his public events?" Elena asked, with only a hint of disapproval.

Caroline caught her tone, and her eyes widened. "Oh, no! Damon isn't like that at all! But, I don't know, I guess it's important to him to stretch out Jess' boundaries. Baby steps kind of thing, y'know?"

Elena simply nodded, but the other woman continued.

"You seem like you're the type who doesn't approve of what we have going on here." She didn't wait for an answer, simply pressing on. "We're all here by choice; we all love our lives with Damon, and each other. We're all consenting adults, and this is how we choose to live."

"And it doesn't bother you at all that the four of you revolve around him? What if you decided to have another boyfriend, what would happen then?"

Caroline opened her mouth to respond, but Jessica arrived at that moment, and the blonde woman fell silent.

Elena continued the interview, on a less tense note, but she wondered what the actress would have answered.

Shortly after the event began, Damon found himself to still be in a bad mood. Even the efforts of his best friend and law partner, Ric, weren't enough to lighten him up. He wasn't in the right mindset to be smiling and enjoying his life when Andie, Ric's sister and a woman he had known for a remarkably long time, was leaving him and moving across the country. Sure, he understood why she would do it; she had told him when they had begun their relationship that her career came first, and a prime post in Los Angeles was nothing to pass up.

Still... Now he was spending his evening trying to see if anyone at the event caught his attention. He was glad to have Rose on his arm. He had known her his whole life, and she always knew how to read his sometimes fickle moods.

"Smarten up," she snapped under her breath at him, "Smile a little, and at least pretend like you're having a good time."

"I am smiling," he answered, grinning at her, smiling wider when she laughed.

"Smile properly; you look like a vampire!"

She reached up a hand, presumably to slap his shoulder, when she suddenly froze, her eyes locked on a point behind him.

"What?" he asked, starting to turn, but she pulled him back to face her.

"It can't – No... But then – My goodness, they could be twins!"

"What?" he repeated, again trying to turn, only to be held back by her deceptively strong hand on his shoulder.

"If you turn around, it will only make your mood worse. I'm warning you."

At that, he couldn't resist. His fingers wrapped lightly around hers, and she released. When he turned, his eyes scanned the room, searching for the source of his girlfriend's disapproval. He found it, and took an involuntary step back.

Across the room, talking to Caroline and Jessica, was his ex-wife, Katherine.

"No," he hissed, "That can't be her." He frowned, counting the days in his head. "She isn't up for parole for another few months."

"Who is she?" he heard Rose whisper behind him.

Damon's face hardened. "I don't know, but I'm going to find out."

And with that, he dropped her hand and began to manoeuvre his way across the room, ignoring those guests calling his name, his sole target the beautiful brunette across the room.

He was practically sweating when he finally made it to the trio, and Jessica smiled softly at him, reaching out to take his hand and squeezing it tightly. He tried to move so that she was behind him a little, feeling defensive at the sudden appearance of his ex-wife's doppelganger at his event.

"Hi," he said breathlessly, extending his free hand, "I'm Damon Salvatore. And you are?"

The stranger's brow furrowed a little, her chocolate eyes narrowing, and the spell was broken. Katherine had never looked that serious, ever. Seductive? Yes. Conniving? Yes. But thoughtful and indecisive? Never.

Finally, the woman extended her hand as well, a tight smile pulling up the corners of her lips.

"I'm Elena Gilbert. I'm here for the New York Times."

He could feel the tension dissipating from his body at the sound of her voice. She was professional, but he could hear the stress lying under her tone, and he wondered what it was about. Katherine had always sounded careless. Already, he decided that the two women couldn't be more different.

That being said, he found himself inexplicably drawn to her. How could it be that a woman who was practically identical to his evil first wife could have randomly shown up at his home? And, he suddenly remembered, on a night when he had his eyes open for another woman live with him?

It wasn't until he felt Caroline's eyes on him that he realized he should be saying something. He was secretly thankful when the bubbly young woman linked arms with Jessica and began to move away.

"We should probably get around to some other guests. It was nice to meet you, Elena!"

"Yeah," the reporter answered, smiling wider and waving a recorder in her hand. "Thank you so much!"

And then they were alone. Elena's eyes drifted back to meet his, and he conjured up his most charming smile. Which was quite impressive, considering the unexpected bout of nerves that had just overcome him, making him feel like either vomiting or kissing her. Hopefully the latter, and preferably not both at once.

"So are you getting all the information that you need?" he asked conversationally.

She nodded. "I'm just doing a recap of the event. I usually report on crime in the city, but I was sick this week, so they gave me something simple."

"The Times, though. That's very impressive. You must be very talented."

An attractive blush spread across her cheeks, but her face remained relatively impassive.

"I work very hard. They appreciate that."

"I don't doubt it." He smiled again, hoping to break down the stiffness in her body. "I believe that you were the one reporting on the Jones case. I was the lead defence."

She nodded again. "I remember. I do my research very thoroughly, Mr. Salvatore."

He felt his eyebrows twitch at her formality. "Please, just call me Damon."

She didn't answer, simply shifted her weight from foot to foot, eyeing the rest of the room, and seeming very uncomfortable.

"Maybe," he began, ignoring the sudden fluttering in his stomach as her eyes refocused on him, "If you wanted to talk about tonight's event, or anything, we could have lunch this week?"

For a moment, Elena seemed to freeze. Then her eyes widened, her brows descended, and her lips tightened.

"Are you asking me out?"

He chuckled a little, and scratched the back of his neck. "Well, yeah, I suppose I am."

Her mouth opened and closed a few times before she could speak again. "With your four girlfriend's in the room?"

The gears in Damon's head began to turn, and he understood his mistake. He raised his hands in a surrendering motion. "Oh, no! It isn't – Well, technically, Andie's leaving, so -"

The reporter looked fully angry now, and Damon took a step back.

"Oh, so just your three girlfriend's then?"

And with that, she turned and started to walk away.

Now typically, Damon Salvatore was the type to just let her go. But not with this woman. She was different, and he couldn't explain it, but he needed to know her. So he followed.

"I don't think you understand, it's an open relationship," he argued.

Elena froze, and turned to glare at him. "Thank you very much, Mr. Salvatore, for your wonderful hospitality, but I'm afraid I really do need to leave. Good night."

As Damon watched her enter the elevator and disappear from his sight, he felt a hand on his shoulder, and turned to meet Ric's eyes.

"What's going on? Who was that?"

"That," Damon answered, turning back to the elevator, "was Elena Gilbert. And I need you to find me everything you can about her."