A/N: Hey guys! This is my first Delena FanFic - There will also be some Klaus/Caroline & Bonnie/Enzo. I'm really excited to finally publish the first chapter, I've had this idea in my head for such a long time but just couldn't bring myself to write it. But here it is! I hope you enjoy it and I would really appreciate it if you could leave a review and let me know what you think/what improvements I could make. Thank you so much for checking it out. There's so many more exciting chapters to come!


Chapter 1

Elena Gilbert swiftly got into her black Chevrolet Malibu, throwing her handbag onto the passenger seat. This was a long week and she was relieved that it was finally Friday. She loved her job, being a lawyer challenged her in many ways and it was never boring: a new day, a new client, a new case. It kept her busy and determined, paid way more than it was necessary and as a result she could lead an expensive lifestyle, live in a beautiful house, drive the best cars and buy designer shoes or handbags. Was that important to her? No, it was just a perk of the job but it was certainly nice not to worry about money or the future. Also, working with her ex-fiancé was a big downside of the job. Especially when you're the one who broke up with him and your best friend is engaged to his brother.

It was 7pm and she had finished later than usual, the firm had signed on a big client and there was no such a thing as office hours when handling a case like this. Luckily it was spring already and the days were finally getting longer, so it wasn't half as bad coming home this late. She took her heels off and threw them next to her purse, finally relieved of the discomfort from wearing them all day. She swiftly wrapped her thin fingers around the tight hair band and let her loose curls fall down her shoulders. She was about to start the engine as she heard her phone buzz.

"Hey Bonnie, I thought you're meant to be on your flight by now? Oh God, please tell me that I haven't been mistaken thinking that it's Friday."

Bonnie chuckled as she heard the distress in her best friend's voice. "I swear you work too much, you are in a desperate need of a holiday. No honey, it's definitely Friday."

A wash of relief came over her body and she instantly relaxed and leaned back into her seat. "Yeah, tell that to my boss. I don't even know what the word 'holiday' means anymore. Anyway, what's up with the flight?"

"Yeah about that, it's not until 2 or 3 am but I am supposed to be sleeping at Enzo's tonight as all my luggage is already there and I can't find my passport anywhere. I think I left it at home, but we're already in a restaurant and I have no time to go back and get it. I was hoping that you'd be able to get for me? "

"Oh yeah of course, I'll be driving past your place anyway. Just text me where you are and i'll drop by once I have it."

"Thank you so much Lena, I don't know where my head's at recently. I'll text you everything!"


By the time Elena had arrived, they had all ordered their food and were sipping on their fine red wine. She'd shown up with a black leather briefcase in her left hand. The long chocolate brown curls cascaded down her back, almost reaching her lower back. She wore a matching crimson suit jacket and trousers, with a pair of black heels and a low-cut black top giving a glimpse of her cleavage. Confidently, she walked up to their table.

A wide smile was plastered on her face as she spoke. "So what do I get for saving your ass" With one hand placed on her hip, she waved Bonnie's passport in the other.

"Oh my God, I love you! You don't understand how much I was freaking out!" She giggled and pulled Elena into a tight hug.

"Ehm, knowing you I think I have a gist of just how much you might have been freaking out." They both laughed as Elena finally glanced at Damon, the handsome blue eyed stranger who seemed to have been observing her ever since she walked up to their table.

"Oh yeah, Elena this is the guy that I constantly complain about aka Damon and Damon this is Elena, my best friend." She gestured at them both and briefly smiled. Damon did not listen to a word of what was just said, having focused his full attention on the brunette standing in front of him, taking up every inch of her feminine figure and those 'fuck me' heels. She definitely was something. And that was anything but mediocre.

Elena laughed reaching to shake his hand. "It's nice to finally put a face to the name. Although I must say Bonnie isn't your biggest fan, so I haven't heard too many nice things about you."

"Well I see my reputation precedes me." Damon chuckled as he took her small, delicate hand into his, shaking it briefly. "I guess I should work on improving that opinion of yours."

Elena playfully smiled and arched her eyebrows in curiosity. Seeing him alone had already improved that opinion, anyone with eyes like his could annoy the hell out of her all day and she wouldn't mind. "What makes you think that you'll get the opportunity to work on it?"

"What makes you think otherwise?" His voice was full of confidence as he spoke.

"You sure are full of yourself" Her lips turned into a smirk, he loved to play just as much as she did. The assertiveness may have come across as cocky, but she loved it when people spoke their mind.

"I don't know about that, but I guess I do always go after what I want." His eyes were fixed on Elena's, his stare penetrated deep into her gaze searching for a sign of approval or maybe a dare so that he could act on his own words. Damon couldn't help but bite his lower lip at the thought of what that dare could lead to.

"Well then I guess you're in for a chase." The words escaped her mouth before she could even get a chance to think them through, but clearly her subconscious mind knew exactly what it wanted.

"Are you presenting me with a challenge?"

She licked her lips in a slow demeanor, completely unintentionally, whilst folding her arms in front of her chest. "I don't know, do you like to be challenged, Damon?"

Bonnie's loud cough abruptly turned their attention away from each other onto her. "Okay, are you guys going to rip each other's clothes off right here, right now? Cause it's getting a bit hot in here, not going to lie."

Boom. The moment was gone, the bubble had been burst. The tension had faded away and left her breathless, it felt like during this entire interaction she had simply forgotten to breathe. Elena also couldn't help but notice her annoyance at Bonnie's interruption, and that didn't sit quite well with her. Afterall, it was just a little flirting, nothing unusual for her, so why did it feel a little different? She quickly dismissed these thoughts. "Way to make things awkward Bonnie." She faked a quick smile.

"Anyway, it was nice to meet you Damon. But I have to get going guys, i'm in for a long ride home and Elijah will be on my case if I don't check in with him in the next 5 minutes." She rolled her eyes at the thought and nervously played with the car keys in her hand.

Enzo shook his head and laughed, as she mentioned Elijah's name."When is he not on your case. You are quite literally the only case he is interested in, I worry about that guy sometimes."

Elena had gotten used to the annoying commentary, but it still rubbed her the wrong way, after all Elijah still meant a lot to her. Just not in the way that he used to. "Don't be a jackass, he's just looking out for me."

"Yeah, you know that's bullshit. He's just waiting on you to change your mind."

"Well that's not going to happen, and we both know that so hush. Seriously, how do you manage to live with this guy Bonnie?"

"Trust me, it's not easy. Come on, I'll walk you to your car." Bonnie grabbed her phone and walked over to where Elena was standing.

Damon glanced over at Elena, definitely disappointed that she was leaving so soon. He couldn't shake off the feeling of slight jealousy rush over him at the thought of Elena calling up some guy who apparently is just waiting on her word. He looked at her one last time and shot a wide grin.

"I guess I'll be seeing you around, Elena."

She smiled and winked at him. "I guess we'll see about that,Damon."


The cold air hit as soon as they stepped outside, it was already beginning to get dark and the chilly atmosphere has set in. It was an unusually cold April evening. As they got closer to the vehicle, Bonnie stood right beside the door, blocking Elena from getting in.

"So, are you really interested in him?" She questioned with a hint of urgency in her voice, as Bonnie was the cautious one in the group. She was the friend that Elena would go to for mature advice or for a shoulder to cry on.

"Interested in who?"

"Damon. You seemed to have hit it off a bit, which I never thought would happen."

Elena let out a heavy sigh, knowing where this conversation was going. "I'm not interested in dating anyone and you know that Bonnie, he's just easy to talk to. And definitely not hard to look at."

"Don't get me wrong Lena, I want you to finally meet Mr Perfect and start going on actual dates. Just not with Damon. He's so not the relationship material and he wasn't lying about getting what he wants, he will seriously try to get into your pants."

Like "Mr Perfect" even exists, she thought to herself. That's what being single for a year does to you. She shrugged her shoulders and replied casually, "Nothing's going to happen between Damon and I. And even if it did, you know i'm not looking for anything serious or for the long term."

Bonnie sighed heavily, in a way expecting this exact response from her. "But maybe it's time to open up to someone, you know to have an actual relationship, someone to come home to. You deserve better than the quick wham bam-thank you ma'am."

"Have you been spending time with my mom lately? Because you sound just like her. I'm fine, seriously, I don't need a guy or a relationship. I've had that before and look what we both had to go through, I just don't want to face that again. If I meet someone who sweeps me off my feet and makes me fall crazy in love then maybe I'll settle. But I'm not actively searching for it, so I'll be okay if that never happens."

"So I guess it's time for Caroline and I to start a search party for the perfect guy? We're allowed to actively search on your behalf, right?" Bonnie grinned widely, happy not to hear a definite 'never'.

"Like you don't already do that, you guys are not as secretive as you think." Elena rolled her eyes. "Okay Bonnie, I've really got to go now. Have a safe flight, be sure to message me when you arrive in London." She pulled her into a tight hug and exclaimed enthusiastically. "Don't stress about meeting the fam, they'll love you as much as we all do."

"Yeah, that's just what I'll keep telling myself. I'll message you, love you." She giggled as she hugged her back.

"Love you too Bonnie."


The normal Friday night did not amount to a lonely evening at home, wearing joggers and an oversized sweatshirt, and a glass of red wine in one hand. It was usually a night out with Caroline and Bonnie and letting the steam off, forgetting all the past worries, but either way it involved consuming too much alcohol and a massive hangover the next morning. Tonight was different for many reasons. Bonnie was flying off to London to finally meet Enzo's family, Caroline was with Klaus, her fiance, planning their wedding. She had hired a wedding planner, but she was doing most of the work herself and Klaus was simply there to nod along in agreement to whatever she decided. Yes, she was one hell of a bossy woman, but he loved her for it and wanted to give her the wedding she had always dreamed, off, so he didn't object to any of her ideas. Or at least most of them, depending on how crazy they were and with Caroline there was a whole new level of crazy involved.

Did it bother her that she was single? Sure, on some level it got to her head. She was a 28 year old woman, two months short of her 29th birthday. Whilst her two best friends were in great relationships, finally finding the man they want to spend the rest of their lives with, all she had was her career. Impressive as it was, recently she found herself missing something in her life. It would be nice to come home and have someone wait for you, to have someone who you can drink a coffee with on a rainy sunday morning. Funny how when once upon a time she had that, she didn't want it. Maybe she was too young to appreciate it then. Either way, it was long gone and there was no going back for her. Elijah was not the man she was in love with, at least not anymore. She couldn't get back together with him just because she felt lonely, it would be wrong for so many reasons. But at times like this, this sense of loneliness got to her and she simply couldn't shake it off.

She unlocked the front door and pushed it open, walking in with a heavy sigh leaving her lips. Shutting the door with her left foot, she placed her keys on the shelf and kicked her heels off. "Home sweet home". She murmured to herself making her way to the kitchen, and pouring herself some red wine. Before she could take a sip and flop down on the sofa, her phone rang. She didn't need to check the caller ID to know who was calling her at this time. "Hey Lijah, I just got home."

"Just wanted to check in, how did the meeting go?" She always loved the huskiness in his voice, and now she didn't quite know how to react to it. It was like a constant reminder of what they had lost.

She propped her feet up on the glass coffee table, as her body sank into the cosy sofa placed in her living room. "Well the guy is a pain in the ass, but eventually we came to an agreement. He gave me all the documents and we've scheduled a meeting for Tuesday morning. But seriously, it's 10pm on a Friday, don't you have anything better to do than worry about work?" She raised her brows, attempting to sound casual.

"Ah well you know me, got plenty of places to be at." He chuckled lightly at the comment. " I didn't like you having to drive back so late, wanted to check that you didn't run into a serial killer on your way or picked up a hitchhiker who decided to kill you in your sleep."

"I think you ought to give me more credit, I didn't go to all these self defence classes to get ambushed so easily. Anyway, I've arrived in one piece so you can stop worrying now."

"If you say so. Have a good night Elena, I'll see you on Monday." He hung up the phone before she could answer.

It's been a year since they broke things off, but he never really moved on. It was always Elena for him, he couldn't imagine being with any other woman and he hadn't really tried. It hurt that she moved on without ever looking back, she didn't exactly try to hide the fact that she's been seeing other guys. None of them were serious relationships, but that's exactly what she needed. After being in a committed relationship for three years she wanted to have fun with no strings attached. Elena was a very confident and beautiful woman, with her olive complexion, doe brown eyes and a body that any woman would kill for, she knew she was attractive. Men never failed to express their interest in her, so she didn't have to seek attention, she received it in the instant moment that she walked into a room.

You'd think that somewhere along the line she'd find someone worth getting involved with on a deeper level, but that proved to be a lot more difficult said than done. She wanted someone who she would lose her mind for, someone who'd make her feel like a teenager with butterflies in her tummy all over again, but that wasn't easy to find. As she removed her makeup and the hot stream of water washed over her body, she couldn't stop thinking of Damon. He intrigued her with the way their conversation flowed so easily. The way his ocean blue eyes traced every inch of her body, the way he bit into his plump lower lip, the huskiness of his voice. Yep, that's what too much wine does to you. God, she really wanted to slap Bonnie for butting in and ending their 'conversation'. But, he did say they'd see each other again and maybe that would happen sooner than he thought.