Chuck: How are things with William?
Serena: Well if I cut everyone out of my life who made a mistake I wouldn't have anyone left.
Chuck: On the topic of mistakes, do you know what one I might have made to cause Blair to cut me off?
Serena: You didn't talk to her after your party?
Chuck: She wouldn't let me in her room. When she said she didn't want to talk to me, I didn't think she meant "ever again." She's not seeing someone, is she?
Serena: No, not unless you count Dorota. She hasn't left her bed in a week.

Serena: Aren't you coming over for brunch?
Chuck: Lily thought it would be complicated enough without me.
Serena: What, my grandmother, my step-father, my father—who was last seen fleeing from the police. Complicated is an understatement.

Serena: Chuck, talk to me. My mom just turned herself in to protect you. Why'd you shut down the party?
Chuck: There's nothing to celebrate.
Serena: What are you talking about? The company is safe, you're about to be head of your father's empire. It's what you've always wanted.
Chuck: What I wanted. All I ever wanted was to know him, for him to let me in. He lied to me until the day he died.

Russell: Don't you even want to know why? Why I was willing to sacrifice my own daughter just to destroy your precious little legacy?
Chuck: Because Lily left you for my father.
Russell: I think you know me better than that by now. Did Reina ever talk about her mother?

Chuck: I'd follow her if I were you.
Russell: No. He signs over the company right now or you're going to jail.
Lily: Maybe. But not because of you or anyone else. I called the DA ten minutes ago. Rufus is waiting in the car to take me downtown.

Chuck: I have guests downstairs.
Russell: And I have the final nail for your coffin. It's just a copy of course. Perjury, obstruction of justice. Bribery of public officials.
Chuck: Why don't we cut right to it.
Russell: That I can do. You sign over Bass Industries once and for all or I'll destroy you and your entire family. I'm surprised you even have to think it over.
Chuck: I wasn't thinking, I was waiting.
Russell: For what?
Raina: For me. He was right about you. This whole time. He was right.

Raina: How many times do I have to tell you, he isn't like you.
Chuck: Maybe not yet. But if I'm right, he's about to cross the line. You can stop him, Raina. You can stop him, Raina. If you care about him, you'll do this.
Raina: I would never confront him based on your word alone.
Chuck: I'm not asking you to.

Chuck: I guess the old Archibald charm wasn't as rusty as you thought. Unlike the knife in my back.
Nate: I talked you up to her like you asked me to. She wanted nothing to do with you.
Chuck: Don't sugar coat it.
Nate: I like Raina. All right? And she likes me. I didn't mean for it to happen this way but it did. I'm sorry.

Lily: Someone who knows about Ben is trying to send a message.
Chuck: Subtle.

Chuck: I came to see Raina. I guess she's not in yet. I wanted to invite her to a party I'm having at the Empire tonight. My deal with Kidd closes tomorrow. You're welcome to come as well. Sorry, I didn't come to gloat. I've just always been a multi-tasker.
Russell: Don't you worry your victory lap might be premature?

The way he's playing this, behind all the false claims there's an agenda. And it's personal. I have to think it's his feelings for you.

Chuck: The slap was a nice touch. Oscar-worthy.
Lily: Yes, well it was surprisingly satisfying.
Chuck: Lily, once again, I'm sorry. I feel like a fool for ever believing Russell over you.
Lily: Well let's just hope it's not long before he's the one feeling foolish.

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.