Present

"So, how is it to finally be an architect?"

The corners of Damon's eyes creased as he grinned at me, and for a small snippet of the moment he looked just like the young Damon that I knew so well; the one that once promised everyone that he would manifest his dream of becoming an architect into reality.

As it turned out, he wasn't completely lying about that.

"It's great, it really is everything that I'd hope it would be." He responded, tracing his thumb along the five o'clock shadow on his face. "Well, maybe minus the long ass days that sometimes never seem to end. So really, not all that different from working in the car garage."

"For what's it worth, I'm really happy that it panned out for you." I regarded him with a small laugh. "Although there were some days that we all secretly wanted to strangle you for never shutting up about it."

"Ah yeah, the good old days when my parents would bitch to you about me behind my back." He chuckled, resting his forearms on the small table.

The change in his posture erased most of the space between us and now that he was this close to me I couldn't stop myself from gawking at least a little bit.

There were so many new things about Damon that I had no way of noticing before; like the sporadic tiny grey hairs nearing the nape of his neck or the small scar right above brow bone. Nevertheless, it was fairly obvious that time had been graceful to him. He was just as handsome as I had remembered.

"It was either that or they were going to send you away, so all in all you got a pretty good end of the stick."

The corner of his lips twitched. "Something tells me that you'd have my back."

"Yeah," I exclaimed breathlessly. "I probably would. I suppose that was always going to be my downfall."

My words seemed to have taken a slight jab at him and I silently cursed myself for letting it slip out.

"You being good to the core and always seeing the good in people?" He swiftly unpacked the buried meaning, his brows slightly furrowed. "If it wasn't for that, there never really would have been an us."

I pursed my lips, briefly dropping my gaze to the napkin in my hand. "Maybe not."

"Do you regret everything that happened between us?"

"Not everything." I mumbled dismissively. "I did have the best summer of my life that year."

"Because you were there with me or did I just happen to be a cherry on top of the cake?" His brows creased as his gaze drilled into me searchingly.

Maybe it scratched his ego or maybe it hurt him to know that I didn't look back at our time together very fondly, but the disappointment was there and it was palpable.

And it was becoming increasingly difficult for me to keep our eye contact as the conversation headed towards the inevitable topic of us and what went wrong.

"I think you know the answer to that."

"Honestly, I don't." He shook his head, looking at me with a wistful expression. "I know that I hurt you, but I never thought that you wished we didn't happen."

A snicker escaped me as I realised that neither did I - a life in which Damon and I never met seemed futile, but knowing that we were never meant to be and that the time we spent together was just a cruel teaser of what could have been but never will be, it made sense.

Deep down inside, it really did.

"You don't know what I had to go through to get over you. You have no idea what's like to lose the person you love."

"What if I tell you that's not true?" He asked with a determination that made me question everything. "What would you do if you knew that I wound up at your door trying to get you back?"

"Damon, please." I pleaded with him not to go there as the wound inside of me threatened to open up.

But then I saw his hand move across the table and gently land on top of mine. "What if I told you that I made a horrible mistake in letting you go, Elena?"

There were many sleepless nights during which I wished for a declaration very much like this one; Damon would have apologised and I would have ran back into his open arms, ready to forgive and forget. That was over ten years ago. Hearing those words today, I wish that I could have brushed them off and let the past be the past. But there was a very small part of me that had been dying to hear him say that… and that small part was getting to me.

"We agreed not to talk about this." My voice was barely above a whisper, as I removed my hand from under his. "I don't want to know why you did what you did, not anymore. I've waited so long for an explanation from you, I needed it to move on. But then I managed to heal and move on without one, so why go there?"

"Maybe I need to say it more than you need to hear it." He sighed, like the weight of the world was resting on his shoulders. He simply looked like a defeated man, beginning to share his final truth.

"I was young and stupid, Elena. I was convinced that I could do everything on my own and be just fine... But trust me, I wasn't fine, not for years after that. And I don't know if that's any consolation for you-,"

"What consolation? I loved you like I never loved anyone in my entire life, Damon and I waited for you! For so long."

I felt a burning sensation in my eyes that urged me to get up and leave, sensing an avalanche of tears that was threatening to spill any moment.

"And to know that you were there, regretting what you've done and in pain over it, is of no consolation for me."

My chest was heaving with anger as I let it all go, finally allowing myself to be angry with him, for once. And through it all, Damon seemed calm and collected, his eyes unwavering.

"I wanted to fix everything, Lena." He broke his silence, sounding apologetic.

"If you wanted to fix it, then why didn't you?" I challenged him with obvious pretence in my voice.

"I tried, although by the time I did you had moved on. And if I'm being honest, I didn't give a fuck about that, because I had hope that maybe despite everything, you still had feelings for me."

I was as still as a statute with a downcast gaze that gave away all my insecurities, because yes.. He was right, so right without knowing it.

He might have lost my trust along the way, but still to this day he held a piece of my heart.

I blinked away the on-coming tears. "What changed your mind?"

"At first? Bonnie sure tried to." Damon released a short, humourless laugh. "She bumped into me and went off on me for being a dick and hurting you, and that you were happy with some other guy. But I told her that I had my mind set on making everything up to you, if you'd only give me the chance. Of course Bonnie was having none of it, but she reluctantly agreed not to say anything to you about seeing me. I wasn't ready for you to know that I came to Chicago."

I was sitting on the edge of my chair with my eyes widened in pure shock, as this was the first that I was hearing about this. Damon being in Chicago, Bonnie seeing Damon, Damon wanting me back.

"And then my dad died." He finished with lips pressed into a thin line. "My world shattered right there and then, and in a whole different way than it did when you and I were over. He had a heart failure, died on his way to the hospital. After that I was a mess. I went down the wrong path, started doing drugs again and it was right around that time that I'd realised you were better off without me."

In that instance I felt the salty tears trail down my bottom lip, realising that I must have started crying at some point. The strain in Damon's voice was too much to bear, and whilst the expression on his face did not give anything away, I realised that he didn't have it as easy as I thought he did.

"I'm sorry that you had to go through that." I wiped the tears away with the tip of my finger, biting down on my lip. "I had no idea that you were ever in Chicago."

"No, of course." He shook his head in affirmation, passing me a tissue. "I was sure that Bonnie would keep my visit to herself, she didn't have an ounce of trust for me."

I took the tissue, sending him a hint of a smile. "Yeah, she always was the wary one in the group."

"Do you mind if I ask you something?" Damon cleared his throat, shifting in his chair which made me nervous all over again.

I nodded a little hesitantly, bracing myself for another blow.

"That guy that you were.. The one that Bonnie said you were happy with?" He looked at me questiongly, like he was testing how far he could go. "Are you still together?"

That caused me to chuckle and I simply shook my head in response, not able to withstand the irony of it all.

Maybe it would have hurt a little less to know that all the heartbreak had its purpose after all, but right then I was struggling to see it.

"Are you married?"

"No."

A moment of silence fell upon us and an uncomfortable feeling of guilt washed over me.

"I mean not yet, I'm engaged."

"Oh, congratulations." Damon paused blankly and then added, "I'm happy for you."

I wasn't sure whether I reciprocated that feeling, but I managed to mumble a small thank you.

"He's lucky to have you." He said quietly with a smile that failed to reach his eyes.

August 2008

"Ahh, I can't deal with this anymore!" I marched in with a sigh and plopped myself onto Damon's bed.

He observed my frustration with amusement, slowly sitting up with the bedsheets loosely draped around his waist.

Today was Damon's day off from working at the garage with Giuseppe, so as soon as I woke up in the morning, I headed over to see him; I wanted to soak up every second that we had left together.

"What's gotten your panties in a twist?" He leaned forward to plant a soft kiss on my parted lips.

"Hm let's see…" I furrowed my brows in contemplation. "My dad's being a douche, Bonnie and Kai have been fighting non stop for the last couple of days and I haven't seen you in like 2 days."

"I know, worst two days of my life." He pecked my nose, giving me a devilish smirk. "And what did your dad do?"

"He's trying to ruin my life, as usual." I mumbled out, thinking back to the phone call that I had with my dad last night. "I'm really starting to think that he'll never get over the fact that I'm not going to college to study Law or Medicine."

"Well, parents usually have a tendency to be disappointed in their children, just ask mine." He added jokingly in an attempt to lighten my mood, but this time it wasn't going to work.

I was angry at my parents for never supporting anything that I did. Well, it wasn't my mum who outright told me that my dreams and plans for the future were childish, but she also didn't stop my dad from saying it. Whilst growing up I'd tolerated it long enough, but now I was struggling to bottle in the plain frustration.

"I'm being serious, Damon. He really said that he has contacts and can get me into any college I want, because apparently it's not too late to change my mind.. Ah, what a jerk."

"I'm sorry." He countered softly, gently stroking my hair. "But you always want to see the good in people and that's what ends up kicking you in the ass, baby."

"But that's my dad, he should want what's best for me." I looked up at Damon with a questioning gaze, like he held the answers to all my questions.

He crooked his head to the side and gestured at me to come over to him, as he lifted one corner of the duvet and shuffled along to make some extra room for me.

I slipped off my white converse and swiftly climbed into bed, resting my head on Damon's chest as he draped his strong arms around me.

His scent had become some sort of a calming essence that never failed to put my mind at ease and I quickly grew addicted to everything about Damon.

"Of course your dad wants what's best for you - but your definition of what that is and his is slightly different." He murmured optimistically, kissing the top of my head. "Ignore him, just focus on what you want to do and he'll come around eventually."

"When did you get so wise?"

He chuckled at my reaction. "Probably right about the time that you and I met."

I responded with a small giggle and snuggled up closer to him. "I guess you're right. I need to stop letting him get to my head."

"As you should. You're insanely talented, Lena. Don't let that go to waste just because other people have a different vision for your future."

"You're just saying that to get into my pants." I pointed out, rolling my eyes.

"I must say, so far it's been working like a charm." He laughed wholeheartedly, squeezing his grip around me. "Now, all jokes aside. You're an amazing artist and don't ever let anyone tell you different, got it?"

"Got it." I whispered with a small smile, as I leaned in to kiss him.

"Now, how did you get in here?" His brow arched quizzically when we pulled away.

"Stefan let me in. He said that your parents went to visit your grandparents and that you're in charge of breakfast today."

"Of course I am." The declaration came out like it was the most obvious thing in the world. "Otherwise this entire house would be on fire from his cooking, or even worse, yours."

My jaw dropped at Damon's mostly baseless accusation. Maybe I wasn't the best cook, but I had my moments.

"Hey, Don't give me that look." He addressed my bewilderedness. "The whole town could smell that burnt chicken you made last week."

"That's because I never used a gas cooker before, and you refused to help me." I reminded him with a grave expression.

"Oh I offered my help, only to get told off for implying that you didn't know how to light the matches." His lips curved into a playful smirk, as he proceeded to climb off the bed and put on a pair of shorts.

"Come on, I'll show you how not to burn pancakes."

I snatched a pillow from underneath my head and threw it in his direction, hitting the back of his leg as he was making his way out of the room. "I hate you."

I heard him laugh it off as he started to walk down the stairs. "And I love you." He called out and although I couldn't see his face, I knew that he was sporting that goofy grin of his.

And I loved him for it.

Present

"Guess that's it, huh?" Damon prodded with an empty stare as we reached the spot where we agreed to meet up earlier in the park today.

We left the café after almost two hours of talking, yet it felt like we were there for just a couple of minutes.

There was so much more that I wanted to say, and so much more that Damon was dying to share with me, but we both reached the point of exhaustion, and just couldn't take any more.

"Yeah, I guess so." I tugged on my bottom lip, finding it hard to look away from him now that we were preparing to go our separate ways.

"Is it too much to ask that we stay friends?" He asked, his eyes boring into me.

I could feel my heart pounding in my throat, the mere thought of Damon being back in my life in any capacity had riddled me with anxiety.

"I can't be friends with you." I sighed sadly, unable to keep up with the appearances for much longer.

"Why not?" There was a hint of sadness in his tone.

"Because I don't know how to be around you and not be the Elena that used to be in love with you."

His lips parted and it looked like he was ready to fight me on this, but then he stopped himself, and all that left his lips was a heavy sigh.

I couldn't fault him for stepping away before too much was said or done.

We both knew this was the end of the road for us.

"Do you at least hate me a little less than you did before?" He pressed, slightly cocking his head to the side.

"I could never hate you, Damon." I confessed with a light smile. "No matter how hard I tried."

He briefly returned my smile, seeming relieved at the answer that I gave him.

"I know that you're not ready for it now, but if one day, you feel like you want to know the full story.. I'll be here."

I wasn't sure if that day would ever come, and if it did, I didn't know if I could handle it.

Sometimes the less we know, the better. For the soul and for the heart. Some things are just too much to deal with, and where Damon was involved… I was weak.

"I will."

"Maybe we'll see each other around sometime."

"Yeah, maybe." I nodded, suddenly remembering that his wife was now working on a project of mine and that would keep us in the same loop for some time.

Damon slowly leaned in and pressed a feather kiss to the top of my head, and I stilled completely. My eyes fell shut and I savoured the entirety of the moment.

"Take care of yourself, Elena." He whispered, before pulling away.

"You too, Damon."

The way back home was a blur and even though my emotions were all over the place, I just simply felt numb. As soon as Damon turned around to walk away, I was gone. It took me less than a minute to hail down a cab and ask the driver to just drive, not caring where it took me.

At first I wanted to go and see Bonnie, because she was my best friend and I had so many questions for her and so much anger that had been brewing up inside of me. But I was in no shape for a conversation and all that would follow in suit. No one knew that I had met up with Damon, and ideally that's how I wanted it to stay.

So after an hour of aimless driving around the city, I finally asked the driver to take me back to my place where I could drown in the solace of my loneliness and preferably some strong alcohol, that I knew I'd find stashed away somewhere in Enzo's cabinets.

With that, the thought of Enzo crossed my mind and I felt that familiar jab of guilt for the hundredth time. I knew how shitty it was of me to be lying to him, so when I got a call from him on my way back home I didn't have it in me to pick and continue lying. So I let it go to voicemail and left his texts unanswered, because I was physically disgusted with myself.

Because the man whose bed I have shared for the last three years, the one that loved me more than anything and wanted to spend the rest of his life with me, was not the man that I spent the entire day thinking about.

Yeah, I know, karma was a bitch and it was most certainly heading in my direction.

Whoever said that it's better to have loved and lost than not to have loved at all knew nothing about love and the pain of having to live with all the 'what if's'. It's the biggest lie ever told - I've been there and done that, only to come out bruised and virtually a shell of the person that I once used to be.

And I say this whole heartedly, having spent the afternoon with Damon, the former love of my life; listening to the sound of his voice, catching glimpses of that familiar spark in his pools of blue, the exact same ones that I used to watch for hours, with an admiration that I was not capable of understanding at such a young age. It was only today that I realised the power of that feeling, when Damon was right next to me, talking to me, looking at me… but he was no longer for me to adore.

Seeing him was a mistake, I knew that now. I should have never agreed to it. I should have never opened that door, even though I had no way of knowing that he was the one knocking. I'd realised that as soon as I came back home and heard the door fall shut behind me. I had no care for the loud noise that it created in the process; after all I was all alone in this empty apartment, and right now I wouldn't want to have it any other way.

Did that make me a terrible fiancée? Surely I'd earned that label as soon as I agreed to meet with Damon. And then each time after that as my heartbeat picked up its pace whenever Damon looked at me in a way that reminded me of the old times.

With the guilt building up again, I didn't hesitate to pull out the most expensive bottle of scotch that Enzo kept hidden away for a special occasion. It dawned on me that the special occasion that he had in mind was probably our wedding day or the day that we'd finally buy our first house together. My mind couldn't be any further from that place today. But I really couldn't bring myself to care about anything at this point.

And in a way that feeling was definitely not new to me.

Suddenly, I was the nineteen year old Elena again and it was like Damon had dumped me all over again. But back then I had all the hope in the world that we would find our way back, though this inevitably slipped away after a couple of months of no phone calls, not even a text message.

Today there was none of that; no hopes of reconciliation, no desire to fix anything. With Damon going back home to his wife and with me making my way back to the cold, empty apartment, it sure felt like the deal had finally been sealed. He didn't choose me nor had I chosen him.

Taking a long awaited sip straight from the bottle, I realised that at last I'd gotten to see that chapter of my life finally closing. Although it was hard to pretend that this was the ending that I'd wished for.

A/N: Hello, finally back with another one! I was so pleasantly surprised with the recent feedback that this story has been getting, I know a lot of you were/are feeling conflicted about this plot so it really makes me happy to see that you're enjoying the story and the characters. This was a hard chapter for me to write, it was emotionally draining, as it usually is with Elena's POV.

As you can see, there's a lot to Damon's story that we do not know, even though he was desperate to share it. I'm planning to share his POV in the next chapter, as we hadn't heard from him directly in a while.

Thoughts so far? I'd greatly appreciate it if you left a review.

Thank you all so much for your support. Take care!