Dan: Hey, what are you doing up here?
Nate: Meeting Serena. You too?
Dan: Why do I feel like we've been here before.

Nate: What's going on?
Dan: Charlie said something that kind of weirded me out. I'm hoping it's just a crazy misunderstanding and not actual crazy.
Nate: What'd she say?
Dan: Well, ah, we were kissing. And then things started to, you know. So then she says, "Call me Serena."
Nate: What?
Dan: Yeah.
Nate: Woah. Are you sure? I mean maybe that's just what you wanted to hear.
Dan: Nice one. But yeah. Yeah I'm sure.

Nate: What the hell?
Raina: Nate. I'm sure you know Jack.
Nate: Yes, unfortunately I do. But why do you?
Jack: I'll be in touch to discuss details. {to Nate} I should have known you'd still be dining on my nephew's leftovers.
Nate: You brought in Jack Bass?

Chuck: So I thought I'd bring some luxury across the river. Brooklyn needs it. It's all bars, bakeries and babies. No hotel in sight. Charles Place. You up to attend the ribbon cutting?
Nate: No thanks.
Chuck: Still pissed I lied to Reina about my father?
Nate: It was a big lie. Even for you.
Chuck: That's why I'm stepping out from under his dark shadow and away from the Bass name.
Nate: Whatever you want to call yourself or your hotel, you're still the same person.

Nate: You don't even know how to be in a relationship. Blair's lucky she escaped you.
Chuck: Hey! Leave Blair out of this. No one understands what we have.
Nate: Yeah, no one understands because it's not normal. She's better off with the French guy.

Nate: Between the video tape you told me about and the letter from her mom. Chuck, I can't let her get her hopes up. She'll spend her whole life searching for someone she'll never find.
Chuck: Don't say anything.
Nate: What am I supposed to do every time she brings up her mother?
Chuck: Lie, I don't know. You'll figure it out. Or just stop seeing her.

Nate: It's four o'clock. It's smoking jacket hour, man. Why are you still in your robe? Is everything okay?
Chuck: Peachy.
Nate: Oh come on, Chuck. I know you've seen the papers. Blair's dating that prince guy. Can't be easy.
Chuck: Nathaniel. I wish my problems were as simple as Blair's royal fling.

Nate: How do you know he's even telling the truth?
Chuck: I don't. But today when that woman wasn't Raina's mother I realized how desperately I wanted her to be. So maybe I do believe it.
Nate: What are you going to do?
Chuck: Try to find out the truth.

Chuck: Russell's parting gift to me was a story about my father. You remember how I told you my dad was responsible for that fire in his old building?
Nate: Uh huh.
Chuck: Russell owned it too. They were partners. He says his wife was there that night. And she died in the fire.

Chuck: Where's Raina?
Nate: She went back to her hotel. I think your whole Howard Hughes routine is starting to freak her out a bit. It's actually starting to freak me out too, man. Talk to me.
Chuck: I saw what you two were looking at this morning. The tattered box, old photographs. Is Raina looking for her mother? It's a mistake. You have to stop her.
Nate: Look man, I know what happened with your mom was painful, but at least you got some answers. Reina deserves the same and she can handle it.

Chuck: Is there a problem?
Nate: With Reina, no. But when you're ready to talk about whatever's up with you let me know.

Nate: Single malt for breakfast?
Chuck: Takes the edge off the coke.

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.