Hello everyone! This fic has been by baby for about 7 months now and I am finally posting it, so this is a BIG day for me. It's a bit different from fics I've done in the past, in a good way, and I'm hoping you'll all like it. This is going to be very angsty, and there's a long road ahead so sit down and buckle up. Reviews would be much appreciated!

Prologue:

A Little Ways Down the Road

Nobody said it was easy

It's such a shame for us to part

Nobody said it was easy

No one ever said it would be this hard

Oh, take me back to the start.

It was a warm June evening in New York City. Elena could feel the moisture gathering behind her neck and she took a rough swipe at it. Her sweating wasn't due so much to the heat as it was her nerves. The hustle and bustle that comes with living in The Big Apple was nothing short of its usual craziness, but at this point it was really just a blur. Her surroundings were almost invisible; there was nothing on her horizon except the high-rise luxury apartments standing in front of her.

She stared up at the tall and intimidating building, then checked the address for the fifth time to make sure she was in the right place. It was a waste, she'd checked enough times to know that this was the correct address, but the more she checked the longer she could stand here and pretend everything would be okay.

She'd dealt with a lot throughout her 23 years of life, but this would prove to be the single riskiest move she would ever make, she knew that for certain, but she needed to do this. She'd spent all those years wondering what would happen when she faced him again and it simply couldn't continue. The constant wondering and questioning was killing her, and she needed to know the truth, whatever the results.

Elena paused, momentarily, and then took a deep breath and forced her body to move forward through the front doors of the lobby before she lost her nerve. The inside was just as intimidating as the outside. The walls were painted a deep crimson and the marble floor was so shiny she could see herself in it. A large balding older man was sitting behind the front desk and she used his current distraction with the newspaper to sneak past him towards the elevators. Having to explain her reason for being here to someone was the last thing she needed at the moment.

Her fingers were trembling when she pressed the floor number in the elevator and as soon as the doors closed a feeling of complete and utter dread took over her body. She'd made it here, she'd come so far, but actually being in the same building as him was paralyzing. This was the only man that Elena Gilbert had ever truly loved. They'd shared something so unique and so special, something she thought would last forever, and yet here she was all this time later talking to him for the first time in years. Suddenly there was nothing between them but secrets and complications. He probably hates me, she thought to herself.

She knew that she had no right to be here, but when the elevator car stopped at her desired floor, her feet carried her through the double doors and towards her destination as if they had a mind of their own. Her fight or flight mode was definitely taking over, and though her brain was leaning more towards flight than fight at the moment, she knew deep down that she needed to fight. She needed to make this right.

She stared at the apartment door as fear wracked through her body. All she had to do was turn around and fly home, pretend that this never happened, and life would go on as normal. He would get to move on as planned and she wouldn't have to deal with whatever laid behind that door.

She made her decision. She wouldn't do it. She couldn't. Could she?

Just as she was about to turn around and abandon her plan the door opened and she was met with those familiar piercing blue eyes instantly. Her heart nearly exploded out of her chest at the sight of him. She couldn't even breathe.

Time just stopped. It was like something out of a movie, it didn't even seem real. She had to blink a few times to make sure her eyes weren't playing tricks on her, but he was there. In front of her. She could see him, smell him, feel him. He looked the same. He was just as perfect as she had remembered and it made her knees almost buckle. Apart of her wished that maybe quite possibly he'd lost at least some of his perfection as he aged, it would level the playing field, but this was not the case. He looked just as beautifully handsome as she remembered. Bright blue aquamarine eyes she could get lost in, flawless porcelain skin, jet black hair that lie tussled on his head just right, and a body any woman would want to climb like a tree.

"Uh, I'm going to have to call you back," he spoke into his phone before hanging up and putting it into his pocket without looking away from her. His eyes were wide with surprise and confusion. Neither of them spoke. Neither knew what to say. It had been almost 5 years.

Speechless. That was the only word to describe his current mindset. This was the girl who literally turned his life upside-down. He'd imagined this scenario so many times since she left. Sometimes she would come back and they'd instantly make up for lost time and end up in his bed, other times he would tell her off until she couldn't take it anymore and he would bask in the feelings of finally getting back at her for what she'd put him through. Now neither of those options seemed appealing.

She looked different. She was still the most beautiful girl he'd ever seen, the face of an angel and the body of a goddess, but she was older. Grown up. She had filled out a little bit, her hair was wavy now, and her features had matured. She wasn't a girl anymore; she was a woman. A stunning one. Even after all this time, after everything she had done, he still found himself completely mesmerized by her.

"Hi…" she spoke softly and just the sound of her voice sent his brain into overload. Her eyes were killing him, pleading with him to give her a chance, and he knew he would end up putty in her hands if she kept looking at him like that. Those big brown eyes held capabilities no one would ever begin to understand. Seeing her like this made it seem as though no time had gone by. It felt like the past all over again.

The problem was that it wasn't the past. It was the present. The past was done, it was over, and no matter how much they both wished they could go back they couldn't. So Damon swallowed back the emotions that were slowly creeping forward and forced himself not to let it get to him. He wouldn't let her inside his head again, or his heart. He'd done that before and it ended terribly.

"I-I-uh-what are you doing here Elena?" He was confused, his voice held the tone of a very very puzzled man, but she could also sense a high level of exasperation in his tone as well. While she'd known he wouldn't throw a party at her arrival, seeing him, seeing the look of disdain on his face, it made her want to break down right there in the middle of the hallway.

Just the sound of her name on his lips again made her want to cry for everything that she had lost with him when she made her choice. Seeing him again made all of the regret that she had tried to run away from hit her with the force of a steam train. Five years of therapy down the drain.

"I wanted to talk to you," she gulped nervously as she looked down at her feet before gathering every ounce of courage she had left to look back into his brilliant blue orbs and at least get out what she came here to say. "I know it's wrong of me to show up like this, especially considering the timing, but I had to."

"How do you know where I live?" He questioned her rather harshly. She cringed at the venom in his voice, but she reminded herself that he was hurt, she had hurt him and he had every right to lash out like this. Especially considering the fact that she showed up on his doorstep with no notice whatsoever the evening before his wedding. He had every right to be angry, she'd expected it. Though it didn't make it hurt any less.

"I-I mean-uh Stefan gave me the address," she rambled twisting her hands together nervously and he frowned at her. She instantly regretted giving him that piece of information considering she was one of the main reasons the brothers no longer had any sort of relationship. They may have never been very close, but she knew that the fact that they hadn't spoken in over 3 years was because of her.

"So he sent you?" Damon scoffed, rolling his eyes as he turned around to walk back into his apartment, leaving the door open behind him. Of course, this was all Stefan's fault. How could he possibly think that Elena actually came to see him on her own? Stefan couldn't get ahold of him so he sent in reinforcements. If he weren't so pissed off he would've been impressed with the balls his little brother had grown since he last saw him.

Elena took the open door as an invitation to follow him and found herself standing in the main room of one of the nicest apartments she'd ever seen. The entire back wall was made of glass and overlooked the New York skyline, a view so exquisite she almost gasped. His old apartment had always impressed her, even if it was rather cold and impersonal, but this was even more magnificent, and also even colder if it were possible.

All of the furniture was dark and modern. It looked like something out of a magazine, a quintessential bachelor pad for the elite. It was just so Damon. He was even dressed the same. Black button up, leather jacket, dark fitting jeans, and his leather boots.

As far as she could tell he hadn't changed much since she last saw him. A part of her had expected he would. He was at that age where men really start to find themselves. She'd remembered her mother telling her that it often took them longer than it took women, and that some men didn't actually become men until their thirties. He was at that stage now, but he was still the same Damon he'd always been. Still the man she'd fallen head over heels in love with all those years ago.

"You know I have no interest in anything involving him so you're wasting your time," he spoke again as he poured himself a glass of bourbon.

"Stefan didn't send me," she assured him as she walked further into his home and closed the door behind her.

Her answer surprised him, not that he showed it on his face. So Stefan hadn't sent her? Now he was intrigued. He sat down on one of the long leather couches with his bourbon in his hand, looking at her inquisitively, and she stood there anxiously as she looked back at him. The tension in the air was so palpable you could probably reach out with your hand and touch it.

Apparently his thing for bourbon hadn't changed either. That was one of the things she remembered most about him, the way he always tasted a little like expensive bourbon. To this day she still got all hot and bothered when she even saw a bottle of it.

"So if Stefan didn't send you, why are you here?" He asked curiously as he looked up from his glass. "It's been over 4 years, Elena. You never called, not once. I spent a year trying to get ahold of you before I realized you didn't want anything to do with me. Now you're just here, in my apartment. I don't get it. You're the one who left me."

"I know," she nodded holding back tears. "I thought I was doing the right thing. I thought it would be better for the both of us if I left."

"That wasn't your call to make!" He shouted, making her jump as he stood up from the couch and ran a hand through his hair. He was already losing control, but that was what happened when he was near Elena. He knew he needed to get his head straight if he wanted this conversation to go remotely well. "I thought that we loved each other and you just left. You didn't even deem me worthy of a real breakup or a goodbye. You just ran away!"

"I know," she nodded again as a few stray tears left her eyes. "The last thing I ever wanted to do was hurt you, Damon! I swear, I thought that I was doing the right thing. I thought it was the best decision for the both of us."

"And what about now?" He asked, sauntering towards her with his eyes narrowed. "Do you still think it was for the best? Because I'm going to assume that you showing up at my door the night before my wedding means you don't think that it was."

"I-I don't know anymore," she wiped away her tears quickly; trying with everything she had not to breakdown completely. "I just-I just couldn't let you get married without telling you the truth."

"And what's the truth Elena?" He asked mockingly. He needed the power that came with talking to her this way. He needed the upper hand. "You have some big piece if information to reveal to me? Well, save it. I don't want anything from you. Not anymore."

"Damon, I haven't stopped thinking about you once," she admitted tearfully. "I did love you, I loved you so much. I still do. You're it for me. There's no one else and there never will be."

She let out a breath she hadn't even realized she had been holding. That confession was partially why she needed to come here. To tell him how she really felt. It felt like a weight was being lifted off her shoulders. She'd gone four years refusing to admit it to anyone, and carrying it around bottled up inside was getting harder and harder. Now he knew and she was being honest, not only with him, but with herself too. Her therapist would be proud.

"You know what sucks about this?" He asked rhetorically, and she shook her head slightly as she wiped away the tears on her damp cheeks. "If you had told me that 2 years ago we would probably be happy right now. We would be together. For the longest time all I ever wanted was for you to come back to me so I could hear you say those words, but you didn't. I changed. I had to. I'm not that guy anymore, Elena. I moved on, and so should you."

"You don't think that I've tried?" She asked him between sobs. "I so badly wanted to be able to move on. I tried, I really did, but every man I ever even spoke to just reminded me of you and what I lost when I left you behind. I hated what I did, I was miserable Damon, I still am! At the time I honestly believed that I was doing the right thing, but now here we are all these years later and I love you just as much as I did before! I love you so much, Damon. I just needed you to know. I know that coming here like this sucks, and I hate that I'm putting you in this position, but I love you!"

"Well stop loving me!" He shouted.

"I can't!" She exclaimed as more tears fell from her eyes. "You act like I can just turn it off, but I can't! Don't you get it? I will always love you Damon! Just you. No one else. It's always been you and it always will be. I tried to fight it, I tried so hard, but I gave up because I just couldn't do it anymore. I'm here because I'm done trying. I'm done attempting to move on from you, it's obviously never going to happen."

"Elena, I'm getting married tomorrow!" He yelled, as he looked at her with wide eyes and the confusion on his face more than obvious. He was so unprepared for this. Apart of him wanted to give in to her, to tell her he felt the same so they could ride off into the sunset together, but he couldn't do that. Life wasn't rainbows and unicorns. Things didn't just work themselves out this way. It wasn't the way of the world. This wasn't a Nicholas Sparks book; John Hughes wasn't off to the side watching in his director's chair.

"That's why I needed to come here," she cried, looking at him almost desperately. "When I heard about the wedding I realized that I'd be losing you forever and I just couldn't let that happen, not if there was still a chance. There's more to it than you think there is Damon, and I have things that I need to tell you before you marry her."

"Elena, I don't give a shit what you want or what you have to say," he shouted, shaking his head back and forth. "When you left I was broken, and it took me years to fix what you made me become. I am finally in a stable place with my job and my fiancé and now suddenly you're here telling me that you've always loved me as though it's going to change something? News flash, it doesn't. You're too late. Snooze you loose. We had some great times and I loved you, probably more than I could ever love anyone else, but we weren't right. You left for a reason, you made that decision because you believed it to be best and now you're going to have to live with it. I'm always going to be pissed at you for how you left things, but you were right to leave. It took me years to realize it, but eventually I did. Our relationship was doomed from the start, we both knew what we were doing and we both knew it was wrong. You're clinging to what we were and I get that because I did it for a really long time, but it's never going to be that way again."

"So you feel nothing for me?" She asked sadly as more tears flowed freely down her face. She couldn't even bear the thought. Even if he was angry, which she expected from him, she'd thought that at least a small part of him had to still love her back. A love like theirs wouldn't just die out. It couldn't.

It pained him to see her like this, which surprised him a lot. He'd spent so many nights laying in bed and thinking about all the things he could do or say to hurt her the way she hurt him, but now that she was standing here crying her eyes out he hated himself for being the person to put that look on her face. He'd always hated seeing her cry, that hadn't changed.

"I could never feel nothing for you, Elena," he whispered, running a hand through his ragged hair again. "There will always be a part of me that loves you, but I just can't do this. Sometimes love just isn't enough. I'm going to get married tomorrow and move on from you for good. You should do the same. Find someone your own age that you can fall in love with, someone who actually wants the same things as you," he smiled sadly at the last part.

It was there. On the tip of her tongue. The one piece of information that could change everything, but as he spoke again it got stuck in her throat. He wanted to move on, and manipulating him with information was wrong. He deserved happiness. She'd taken it away from him once and she couldn't do it again. He didn't love her, he didn't want her, so why should she lure him back to her by telling him something he wouldn't even want to hear?

"You deserve better than me anyways, you always have. I'm not a family man and I'm married to my job. You deserve it all. The white picket fence and the family. I can't give you those things." He frowned looking down at his hands before looking into her eyes again. "Besides, when you had that pregnancy scare you told me that all you ever wanted was to be a mother, but I don't want kids, I never have. I would be a terrible father. We don't want the same things out of life Elena, we never have."

"You're right," she finally said wiping away the last of her tears. "I guess I just couldn't let you go through with it until I spoke my peace. I really do hope you're happy Damon," she forced a smile before she turned around and walked away.

The door slamming behind her gave the situation a sense of finality. As she made her way down the long hallway in his apartment building a small part of her wished that he would come after her, even if she knew that whatever chance they had just ended. He wasn't going to chase her. They wouldn't share a passionate kiss and run off together.

When she made it out of the building and down onto the street everything hit her like a freight train. He rejected her. He disappointed her. This trip was a waste of time. All it did was reassure her of everything she was most afraid of. Worst of all, she chickened out and didn't tell him the truth.

But she couldn't. She couldn't do that to him. She'd done enough damage already. He wanted to get married and live his life, and she was going to give that to him.

She dried her tears and hailed a cab to the best of her ability, it took her a few tries, but finally one of the yellow vehicles stopped for her and she hurriedly got inside, hoping to get back home as quickly as she could. She'd never been to New York, but she'd always wanted to. It's funny how when she finally made the trip it ended up being the single most heartbreaking experience of her life.

"Where to Miss?" The driver asked once she'd made herself comfortable in the backseat.

"J.F.K.," she mumbled, resting her head against the cool glass of the window. She could see all of the people walking along the sidewalk, living their own lives and she envied them. They were probably normal. They probably lived normal lives and she wanted that.

"You going on vacation or something?" The driver asked as he took off down the street, trying to make conversation.

"No, I'm going back home," she sighed, forcing her eyes shut and using every ounce of strength she had to keep the tears at bay.

"You were in the city visiting then?" He asked, smiling politely at her through the rear view mirror.

"Something like that," she mumbled, wiping away at one rebellious stray tear.

He was only trying to be nice, she knew that, but at the moment she didn't have it in her to be nice back. She'd left behind the only man she'd ever loved. The only man she wanted to spend the rest of her life with.

The man that fathered her child. Not that he knew it. He was a father and he had no idea. Their son was snuggled warm in his bed back in Los Angeles right now, so innocent in all of this, and it made her cry even harder.

As the driver quietly continued along the busy streets of New York City all Elena could think about was how badly she'd fucked up. Not just today, but with everything in her life. She wanted to go back. She wanted to change the outcome, but that wasn't possible.

Life is filled with choices and regrets, and now all she could do was look back on them and wonder what would've changed had she gone down a different path.

Well there we are. The next chapter is going to jump back and we'll relive their journey from start to finish. And YES, we will get to the prologue and find out what happens after, eventually ;) In the mean time leave me reviews and let me know what you think.

Until next time, my lovelies.

-Emily