Based around Chapter 10 of The Awakening, more or less in Damon's point of view. Kudos to L.J. Smith for the scene (and the whole series, frankly!).
Do you remember the first time we met, Elena?
I do.
I'd seen you before. You don't know it, but I had. While you were outside your house; with that boy; in the graveyard - I'd been watching you. You were fascinating. You looked like her; Katherine. That beautiful girl I'd lost so long ago. I'd thought she was dead, but we all know how that turned out. It would have been better if she had died. Still, I'd loved her, all those years ago. And you looked like her. That gorgeous, silky blonde hair and those eyes the exact shade of lapis lazuli. I knew my brother was interested in you, and you were interested in him. And I knew you were different to Katherine. Fiercer, bolder and much more independent. But I had to speak to you.
I suppose my curiosity just got the better of me, that night. You were alone, apart from those two other girls - the little bird and the dark haired temptress. Apart from them, the hall was empty, and no one would have to know I'd seen you. At the time, I thought it would just be once. One look, one talk, one goodbye. Then I would leave. You weren't Katherine. You never were. So what was there to pull me to you? I could leave, and keep an eye on my brother later. But things changed.
You were amazing. I can admit that. Not out loud, and never to your face. But I can admit it to myself. You were strong and spirited; I could see it in your eyes. At first you were afraid. But then, you were like a cornered tiger. You challenged me. I was right - you could never be Katherine. You wanted to know how I had gotten in there, into that worn, dark gym hall. Of course, I was never going to admit the whole truth. That I had tripped the power to send your friends running; that I had set it all up so I could have just a few minutes alone with you. But I did tell the truth. I had come in through the door. And you were right - it had been locked. The fact it wasn't anymore was beside the point.
I knew you were mad at me, either way. And then you spoke of the dark. My reply, again, was true enough. Interesting things do happen in the dark. After all, I gave myself over to the darkness in Florence all those years ago. So many things lurk in the darkness, so many things you would never have understood - things you probably wouldn't understand, even now. But you were the most interesting of them all, in that moment. I couldn't take my eyes off of you. You were intoxicating. I can never say it, never show it - but you were.
You wanted to know if I was looking for someone. I afforded myself a small, sweet smile at that. If only you knew. But soon enough, I found myself attracted to you like a magnet. When I had come, I swore it would only be one talk. But you were so tempting, so glorious in your passion, your anger and your fear. And you were so beautiful. I couldn't stop myself. And neither could you. I could see it in your eyes. I didn't use my Power; I didn't compel you. You might think I did, but I never even tried. I wanted it to be real.
But then you snapped out of it. I could have pulled you back. I could have tried to influence you, but I didn't. I couldn't bring myself to. I knew in that moment I wanted you. I was wrong when I thought I could walk away from this. But I couldn't use my Power to get you. The victory would only be worth it if I could do this alone. You weren't meant to be one of the hundreds I manipulated into being with me. You were meant to choose me yourself. But in that single moment, I knew what I wanted. I hadn't felt like that for centuries. I hadn't felt like that since Katherine.
Then you said you were leaving. I didn't want you to, but I had to let you go. You were trying to fight me. You were trying to be strong, independent and you were trying to stay faithful to my pathetic little brother. You had more spirit than Katherine ever had. She never would have walked away. She never would have questioned me the way you did that night. She never would have done half the things you did. My brother wouldn't know what to do with you. I was sure of it. At that moment, I could just imagine you, standing proud and glorious in immortality, my princess of darkness. I couldn't leave town now. You were my challenge and my ultimate prize. I wasn't going to let you go without a fight.
I watched you leave, through the darkened hall. I waited until the last moment for my parting words. I knew I'd shaken you with them, but I wasn't sure I cared. I had my goal. I wanted to succeed. I didn't know then how hard it would be. I didn't know then that I would fall for you so completely. I didn't know then all the things you'd get me to do. And I didn't know then how many times you'd break my heart. And they wonder why I am the way I am. They wonder why I chose the darkness.
I can never tell you any of this. Not now. Not after everything we've been through. I can't bring myself to ruin you like that, Elena. We tried to make Katherine choose once, my brother and I, and look what it did. It tore her apart; it turned her against us. It made her a monster. I can never truly make you choose, and I can never tell you any of this. But I need to say it somewhere.
I need to tell you I love you.