PI: Your dad gave me these security tapes after the huilding burned down and asked me to lock them away. This one is from 8 p.m. the night of the fire.
Chuck: What's on it?
PI: Bart. having an argument with a woman. Avery Thorpe. Then Avery goes into the building and Bart hurries away.
Chuck: Okay. So?
PI: Moments later the building goes up in flames. And Avery Thorpe is never heard from again.

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: Do you want me to come along? I know we've been on opposing teams for awhile, but... I've been through this. Maybe I could be helpful.
Raina: Actually, yeah. I'd appreciate that. I really hope it's my mom, Chuck.
Chuck: Me too.

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.

Chuck: You don't have to be powerful on your own first. We can build our futures together.
Blair: The saddest part is that I'd come to the same conclusion. But now that I know I'm ready I realize you're not. I mean, after everything you went through—Prague, Eva, Russell—that maybe you'd changed. Who was kidding.
Chuck: Don't say that.
Blair: You have years before you're capable of a real relationship. If you ever will be. I'm sorry Chuck.

Blair [to Chuck]: Because it made me realize I wanted to be with you. Dan and I both know it meant nothing—less than nothing. Right?
Dan: Yeah, that's right.
Blair: I was going to tell you all about it tonight. But that would have been a huge mistake. Dan Humphrey may not be royalty but at least he's not a child.

Blair: Are you trying to humiliate him? Is that it?
Chuck: I don't care about him one way or the other. I just wanted you to see he's not a part of this world. I know you kissed him.
Blair: So? You and I are not dating. And you kiss a lot of people.
Chuck: You're not supposed to kiss him. He's hum-drum Humphrey. Epperley told me it was life-changing.

Chuck: Did you notice her talking to anyone? Whoever she kissed seems to have had an effect. "Life-changing" were the words she used.
Dan: Well a life-changing kiss might not be something you want to mess with.
Chuck: What are you trying to say, Humphrey?
Dan: With you, she was always caught up in schemes and takedowns. But that's not really her. She's intelligent, she's intuitive. You know? She weeps when she watches Nights of Cabiria.
Chuck: How do you know that?
Dan: Uh... Serena told me. But listen, if Blair's happy, I mean maybe you should let her be.
Chuck: You care more about Blair's happiness than I knew.
Dan: Eh.
Chuck: Thank you for your time.

Dan: Hey Chuck. Uh, what are you doing here?
Chuck: May I come in?
Dan: Yeah.
Chuck: I've learned some information about my past that's making me reconsider my future. My future with Blair. However my intel indicates that she's seeing someone else.
Dan: What's that got to do with me?

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.