Nate: Serena? What happened?
Serena: Where's Tripp?
Nate: Tripp? Tripp's not here!
Serena: He was driving ...

Nate: You have two options. One. Man up, go to war and fight for the girl you love. Or just forget her. Move on to a palette cleanser. And forget her.
Dan: So you're saying my only choices are extreme emotional vulnerability with a good friend, or meaningless sex with a stranger.
Nate: Pretty much.
Dan: Alright.

Nate: Dan, do you really think if you went toe-to-toe with Paul Hoffman that you couldn't take him? You're using him as an excuse.
Dan: No. He's a handsome guy. He's a sophomore. He and Vanessa have a lot in common.
Nate: He's a douche.

Nate: Don't go with Tripp.
Serena: Nate ...
Nate: Look, I know what I did was wrong. But I did it because ... ever since last week, ever since three years ago when you left ... please don't go. Please stay here with me. Please give me a chance.

Nate: Someone's gotta get through to her before it's too late.
Chuck: You know Serena. Whoever tries better bring a sledgehammer.

Chuck: I just came from a meeting with hotel security. Elevator cameras caught someone pulling the emergency stop button to have a makeout session with their boyfriend.
Nate: You just love your job, don't you?
Chuck: It was Serena and Tripp.

[to Dan] I told you this would end badly. Threesomes, man. Don't believe the hype.

Nate: Oh my God. This is NOT your next story for the New Yorker. I'm sending it out to an entirely different magazine.
Dan: Oh thanks. That really helps.

Affairs with married people, threesomes, it just so happens everyone's problems are within my area of expertise.

Nate: Serena, I didn't tell you about Maureen because Tripp's a married man. If you go with him now you're going to cross the line.
Serena: Thank you for everything, Nate. Really. But that line just got a little blurry.

Nate: Two years ago at the masquerade ball, I tried to tell you I loved you. But I told Jenny Humphrey. She was wearing your mask.
Serena: You loved me?
Nate: Of course I did. You were the most beautiful, alive person I've ever known.

Nate: Give me the phone. You can't talk to him, you can't think about him until his plane leaves.
Serena: What are you gonna do, tie me to a chair?
Nate: I'm gonna take you on a pub crawl, and we're gonna get drunk. Like REALLY drunk!
Serena: Okay!

Gossip Girl Quotes

Even Blair Waldorf can not bend DNA to her will.

Dan

Hazel: Do you know what you're doing, Little J?
Jenny: I'm not Little J anymore.