Damon: Every time I look at you all I see is NOT Elena.
Bonnie: I'm so sorry this happened, but I lost Elena too, Damon. And you're one of the few reminders I have of her to hold on to so you can either resent me or love me, but you're stuck with me.

Dear Diary, I'm in Hell. It's hard to imagine a place worse than where I've come from but by some spectacular miracle, I've found it. In the weeks since I've arrived, three things are clear. The food is literally made of poison, the air smells like a plague, and everyone wants to know what everyone else is doing. I don't fit in here. The world is not what I imagined.

Valerie

Stefan: If you think this is a crazy plan, now's the time to speak up.
Caroline: Is there any version of this plan where you're not worried about me?
Stefan: Probably not.

Damon: If Stefan says he's got it, he's got it.
Bonnie: Do you really believe that or is that just some excuse to continue your slow crawl towards rock bottom?
Damon: Do you know how many days need to tick by before I see Elena again? Twenty-two thousand, nine hundred and sixty one days, and that's if you get some old person's disease. I have not even begun to approach rock bottom.

Stefan hangs up his hero hair for the girl. And here I thought my future was bleak.

Damon

Pick a side, Enzo. Us or them.

Caroline

Bonnie: Do you have any idea how long three seconds are in a life or death situation?
Damon: In the first second, I thought how amazing it would feel to have Elena in my arms again. By second number two, I had kissed her. And by the third, I remembered you're my best friend and that if anything ever happened to you, I would lose my mind. So yes, Bonnie, I do know how long three seconds are.
Bonnie: Just checking...
Damon: I will wait for her. And you're going to help me. You're stuck with me too.

So Damon screws up, Caroline gets grabbed, and I get to wind up dead? Doesn't it ever feel like we're fighting the wrong enemy?

Matt

Alaric: You wouldn't think it's weird that I'm trying to contact my fiance who's been dead for months?
Bonnie: Honestly, after everything we've experienced, it'd be weird if you weren't.

Enzo: I'm not here to be one of your children, Lily.
Lily: Then why are you here, Lorenzo? Why did you choose us?
Enzo: There was no 'us' in my choice. I choose you. I'm here because of you.

Stefan: You killed him, didn't you?
Damon: Tyler? No. Jeremy once, but are we really bringing that up right now?

[to Bonnie] So, about how long do we have before this evil engulfs the world? I'm just trying to plan my week.

Damon

Vampire Diaries Quotes

Oooh, you know I don't know. Every time we try and go on a date you get kidnapped, I get sent to a prison world, or your feelings get compelled away...

Damon

Damon: My new girlfriend. Andie Starr. Action News.
Alaric: It's not called Action News.
Damon: I know. I like just saying it.