Thank you guys for the great responses on the first chapter! I am so glad that people are enjoying it who haven't even read or seen the play! I hope you all continue to enjoy it and keep writing me reviews. Metaphorical cookies to the Anon who simply wrote, "update". Best review of the bunch.


"Caroline, you just have to come with me! You know I don't understand any of that business stuff. Plus, consider it networking. When you are out in the world trying to make it in marketing, it might be nice to have Damon Salvatore as a reference, just saying," Elena said as she applied a coat of lipgloss. Both of the girls had Thursday afternoons off, and since the dinner they had the week before, Damon had been calling Elena constantly. Finally she agreed to meet him, but only for an office tour, nothing more.

"Yeah, yeah, you're right. This time at least. Heard from Stefan today?" Caroline said as she put her wallet and keys into her purse.

A large grin took over Elena's face and her eyes lit up at just the mention of his name. "He texted me this morning, but he still hasn't asked me out. It's against company policy, he would have to go and get permission from Mr. Mikaelson to do it so I think he's waiting."

Caroline nodded as she wrapped a light cardigan around herself. She could understand the hesitation, but the two were practically dating already. Elena had seen him almost every day, and they were texting constantly. She knew that her friend was already head over heels for the guy, and she barely knew him.

"I don't see why that's such a problem, I mean, you two are basically dating already, you are constantly in contact with you and you've had dinner together what, twice this week?"

"It's not official, so don't be going around saying that it is. I don't want him to get in trouble or anything."

Caroline rolled her eyes as the two girls headed out the door, making sure to lock it behind them. The trip to the office was a short one and Caroline parked her cheap blue sedan in the special place reserved for the Gilberts and followed Elena into the office complex. No one was really quite sure what the Gilberts Trust actually did, from Caroline's knowledge they basically bought and sold commercial properties and small businesses, but she didn't really know exactly how that was done.

Heading to the twelfth floor the two girls made it to Damon's office. He flashed a smile at Elena before he noticed that she had brought her best friend with her. Disappointed he had to think quickly about how to get Elena on her own, and to rid himself of the tag along. Damon started the tour and after passing a few offices stopped at the one that Klaus and Stefan had been sharing. "Caroline, I remember you saying at dinner that you were interested in marketing. My brother just finished working with and advertising agency in New York, you should really ask him about it. I'm sure he'll be back any minute."

Elena looked over and frowned, noticing the obvious attempt that Damon had at ditching Caroline. Caroline gave a small shrug to her friend and stepped into the large office. "Actually maybe he can give me a few ideas for my upcoming essay, what a great idea, Mr. Salvatore."

Damon nodded before looping his arm around Elena's and pulling the brunette away. Caroline took a seat behind one of the desks in the office and placed her feet up on the desktop. It was a rather comfortable chair, leather and the gave her the support she needed. She took the time to look around the room and to snoop on the possible next boyfriend of her best friend only to notice that there were no pictures at the desk she was seated at. Instead their were drawings and on the wall behind her a landscape painting that she wasn't familiar with.

"So you decided to give me a call after all," she heard a voice say behind her.

Caroline looked up to see Klaus standing against the door frame, arms crossed with a smirk plastered on it.

"Can't say I imagined this particular scenario, but I also say I don't mind it."

Caroline rolled her eyes. "I'm waiting for Stefan, so don't get your hopes up, love."

"Considering he is in meetings with John Gilbert all day, you might be waiting for quite awhile. Elijah likes to bring his little prodigy everywhere with him. It's like the puppy we had as children."

Caroline could hear the resentment in his voice. For as much as the Stefan and Klaus were friends, which they obviously were for some reason or another, Klaus didn't like the fact that Stefan was favored by his brother. "What, you're not the shining star in the company? I would have never guessed."

"Work is a foreign concept when you are raised as we were. My brothers and I were raised in luxury. Elijah was the only one that had any sort of interest in business. I am only here because my father forced me to. This or lose my inheritance. I work as little as possible, so no, I'm not really employee of the month material."

Growing up in a small town by a single mother had not given Caroline all of the luxuries that Klaus was speaking of. She was working from the time she was sixteen, before that she was a babysitter, anything to get a few extra dollars so she could have some freedom. It used to bother her how easy Elena had it, money just pouring in, but Caroline came to understand the importance of hard work. People like the Mikaelsons and the Gilberts, they would never get that chance.

The more she came to learn about Klaus the more she disliked him. She tried her best not to judge people based on social class, but he was starting to become the definition of privileged lazy youth. "So let me guess. You have homes in New York, Los Angeles, and judging by your accent London. You went to an elite university where you slacked off and still managed to pass with decent grades and now you just waste your time swindling failing businesses out of their money?"

"You forgot the bit where I charm women to sleep with me by informing them of my wealth, but you have the general concept," Klaus said as he walked over to the desk.

"Why are you sitting there? Go sit at your own desk," she said pointing at the desk in the opposite corner.

"You're in my desk. That," he said referring to the other desk, "is Stefan's desk. If you would have even bothered to check you would have seen it full of family photos and pictures of his college friends."

Caroline picked up one of the framed drawings and showed it to Klaus. "Who did this?" she said.

The sketch was of a field, with wild flowers growing on a shallow hillside. "I did," Klaus told her. "It's one of my favorite spots, actually. Just outside my gran's house in Dorset."

Caroline was interested, but still not completely sure what she thought of Klaus. She was still quite taken aback by his aggressive nature at the bar, and his passive attitude towards life, but looking at the drawings she could see there was something else to him as well. "Do you ever draw people?"

"Occasionally. Given the right model."

Caroline knew that she was heading down a risky path with her questioning but she just had to know. "Like a woman you fell in love with?"

"I have a strict policy when it comes to women. I don't fall in love and I don't plan on it. Love turns men into saps. Look at Stefan if you need any proof. Not even properly dating the girl and he's already talking like a madman."

"You don't believe in love. I speak for all of my gender when I say that's a relief. The last thing that the world needs is men like you breaking women's hearts. Women around the world are rejoicing this very instant!" Caroline said with a smirk.

Klaus turned and looked into Caroline's eyes. As much as he could tell she was just trying to bother him he saw something else too. "You don't believe in love, do you?" he asked.

Caroline tilted her head to the side, confused at how he was able to figure that out about her. "I'm not sure about that, necessarily. But I do have to wonder if it's really everything people make it out to be. These stories tell girls that their life won't be complete until they meet some handsome man that will sweep them off their feet. That's just a lie. You can have a full and complete life without all that crap."

Klaus nodded, agreeing with her statement. She had a point, the idea that people were missing 'other halves' always seemed rather ridiculous to him. "So no men in your life? Let me guess… you have a cat."

Caroline gagged. "I hate cats. I am much more of a dog person. And I never said their were no men in my life, I just said I don't do love. There's a difference there. I'm twenty-one years old, I'm hot and I like to party. There are definitely men in my life, I just can't necessarily remember their names in the morning."

Now Klaus was intrigued. She sounded a lot like a female version of himself. Except for the fact that she was rather sarcastic, a quality he generally didn't like in women. He was about to tell her his opinion on the brief encounters when Elena came bursting into the office to see Caroline in the desk chair and Klaus very close to her, leaning against the desk, an apple in his hand. "Ready to go? I have to be back on campus at four, I promised Bonnie I would meet her to discuss our teaching plans."

Caroline almost leapt out of the chair and hurried over to the door. "Yeah, I really should stop by the library, I have that project due in a couple weeks," she lied.

Elena raised an eyebrow but didn't say anything. The two girls walked out of the office and Elena waited until they got into the car before telling Caroline about what had happened to her.

"Oh my god, Caroline. I can't believe you left me alone with Damon!" Elena exclaimed.

Caroline shrugged as she started the car and backed out of the parking space. "He didn't really give me much of a choice. And it wasn't like I was given great company either. Stefan was in meetings all day, so I got left with Klaus. What happened anyway?"

Elena shook her head and took a moment to gather her thoughts before telling her friend the story. "Everything was fine, he was just showing me around the office and explaining exactly what the firm was doing for my family. At the end though, he shows me his office, right? Then he proceeds to shut the door and close the blinds! He came towards me and I ducked under his arm and out the door so fast… But then I ran into Elijah and had to talk to him for a bit before I could find you."

Caroline wasn't surprised, her friend always tended to get into these kinds of situations. And she had noticed the predator look in Damon's eyes when he had tried to get rid of Caroline earlier in the day. "I'm sorry, Elena. But think of it this way, I think he got the message that you aren't interested now."

"Yeah, I would hope so," Elena said with a huff.

Jenna, leaving the office of the Gilbert Trust for the day slipped into the elevator unnoticed. She slipped behind the businessmen in the nice suits and leather briefcases and waited to get off on the ground floor.

"I spoke with John Gilbert about it this morning," the taller man said to the darker featured man. Jenna had been looking down when she entered the elevator and hadn't seen the faces of the men. "He gave the okay, saying that Elena's personal life could remain separate from the business, as it already was."

"That must have been a relief," the other answered. "I know you were worried about what would happen if the heir from the firm tried to date a client's heiress."

"It's against policy, that's all," Stefan replied. "But this isn't like the other girls, Tyler. She's different. She's sweet and compassionate. I don't think I have ever met anyone with a heart like hers."

"Plus she's hot as hell," Tyler laughed.

Stefan shook his head and chuckled. "Yeah, there's that too."

As the doors opened the two men parted ways and Jenna tried to get a glance of their faces. She could connect some of the dots but she wasn't sure if she was correct. It hadn't sounded like Elijah's voice in the elevator, but she could tell that it wasn't Damon Salvatore, the hair color was too light. Racing home she told Alaric what she had overheard, convincing herself as she told the story that it must have been Elijah that had feelings for her niece.

"That does seem a little hard to believe, Jen," Alaric said over dinner. "I mean I saw them at the dinner, I didn't really see anything that would make me think the man thought of her that way. Plus, think of the age difference! Elena is what, twenty-one now? Elijah is almost thirty."

"That's just what I saw," Jenna stated plainly. "I think I should call Elena though, warn her."

"Warn her that a man is going to ask her out on a date? She's an adult Jenna, I think she can handle it on her own."

"Fine, I won't then," Jenna told her fiancée.

"My brother told you this?" Damon asked Tyler, his voice rising with anger. "How does he even know the girl?"

Tyler nodded. Being Damon's assistant meant that he had been through his fair share of Damon's temperamental moods so he knew that he just needed to remain calm and tell the truth. "They met one of our first nights in town, at a bar. Been talking pretty much all the time since. Stefan hadn't said anything until today because he didn't want to risk the firm in any way."

Damon grimaced and thought about the encounter that he had had the day before with Elena. If she had already had her sights on his younger brother, that might explain why she denied his advances. Damon was sick of his all-star brother who always seemed to have everything handed to him. Damon had worked hard, tried his best to show their father that he was worth his love and appreciation only for Stefan to come in and steal the spotlight. This girl was just another example of how Damon would continue to lose against his brother.

"You liked her," Tyler could tell just by the look on his employers face.

"Yes, I did. I tried to win her over myself yesterday, only to have her duck under my arm and slip away. It was embarrassing."

Tyler tried his best to hold back a laugh, knowing that it would only lead to a violent outbreak from Damon. The image of the small girl pulling herself away did prove to be amusing though. "What are you going to do about it?"

"What do you mean, what am I going to do about it?" Damon said as he walked over to his desk. He pulled open one of the file drawers and reached into the back where he held his best whiskey and glasses. Pouring himself and Tyler a glance he waited for his answer.

"You're just going to let Stefan have the girl? Sounds like giving up to me, that's all," Tyler answered as he grabbed one of the glasses and took a swig.

Damon thought it over for a few moments before making his decision. He was sick of Stefan getting everything in life. Although he wouldn't try to steal Elena from him, he was past that given the way she had dodged him, but he would make sure the couple didn't succeed. His younger brother needed a little heartbreak in his life.

"I see what you're saying, and I am willing to consider some possibilities," Damon said as he downed his drink. "You agree to help me with this and you won't be an assistant for much longer. What do you think?"

Tyler finished his own drink and set it down on the desk. "I am sure we can think of something. Now I have a date with a local to attend to. Don't drink yourself into a coma while I'm gone, I hate having to pick you up at the emergency room."

Damon waved him off and poured himself another drink before sitting down at his desk and looking over the files for the Gilbert Trust. It was going to be a messy deal when things were all said and done from the looks of their financial reports and Damon wanted to be the one that found the missing link. Also being alone gave him the time and opportunity to figure out what he was going to do to sabotage his brother's new romance.

"Ugh, Rebekah has someone over at her apartment tonight," Caroline moaned as she dragged a blanket and pillow into the living room. "For as much as we pay for this place you would think they would have some thicker walls."

Elena shrugged as she looked up from her homework. Having been distracted so much lately by Stefan and trying to see him that she hadn't been getting most of her assignments done. The phone next to her vibrated on the table and she picked it up with a smile.

"Stefan?" Caroline assumed.

"Yes, and it's news for both of us, actually."

Caroline perked her head up, now interested it what was going on. She sat down on the smaller of their two couches and started to position herself for her night's sleep. "What do you mean?"

"The firm and the Trust are throwing a charity event next week. One of those fancy balls, a masquerade," Elena explained. "No dates though, no one is supposed to know who anyone else is."

"Interesting…" Caroline said as she laid her head down on the arm of the couch. "I wonder what the point of not knowing who people are is though…"

"Probably some sort of money raising scheme. Like that one we went to last year where anytime you said the word fundraising you had to give twenty dollars," Elena said as she texted her reply.

"Yeah I bet you're right. Are you going to be here awhile, because I have work in the morning and you know how loud Rebekah can be…"

"I'll get up and move right now. Night, Care."

"Thanks, night."


Are you ready for a masquerade ball? That's where the fun really begins! I am sorry to my fellow Damon fans (I am a huge Damon fan myself) but he representing the villan for the course of this fic, so I hope I can do him justice even though he's not our sacrificing brooding tough guy.

Still waiting for someone to guess who the characters line up to! Reviews are nice, but feel free to leave questions or comments on my tumblr as well (riverssongs). See you soon!