Blair: I hope never giving up on people isn't going to be my downfall.
Chuck: That's why you're going to be an amazing mother. You're always there for the people you love. Even when they don't deserve it.
Blair: You know that's never going to change.
Chuck: It's okay if it has to. Starting tonight I'm going to take care of myself.
Blair: Is that all?
Chuck: Yeah.

Chuck: I'm sorry for losing my temper the night you told me Louis proposed to you. I'm sorry for not waiting longer at the Empire State Building. I'm sorry for treating you like property. I'm sorry I didn't tell you I loved you when I knew I did. Most of all I'm sorry I gave up on us when you never did.
Blair: Thank you.

Blair: Then what are you here to apologize for?
Chuck: Everything else.

Blair: What are you doing here? I don't have the energy to rehash tonight's hysterics. I think you should leave.
Chuck: I'm not here to apologize about what happened tonight.

Dr. Barnes: You chose to let go. Continue down that road and I'll bet you find some peace.
Chuck: I've always wondered what that's like.

Dr. Barnes: I understand you're angry. I don't expect you to ever forgive me. I just thought you should know Louis wasn't paying me for information alone. He wanted me to drive you into a rage. To turn you into this monster you apparently used to be. Louis is so threatened by you that he wanted to remind Blair—
Chuck: Why she chose him. Maybe Louis' right.
Dr. Barnes: He doesn't have to be. You can change.

Dr. Barnes: You have to face that you didn't let Blair go, you lost her. To someone else.
Chuck: You don't know what I did. But yes, maybe there is something I need to do if I'm ever going to move on. I don't want to lie to you, I don't want to lie to myself. {he retrieves the Harry Winston engagement ring} If I've really let Blair go, I don't need this anymore.
Dr. Barnes: It's beautiful.
Chuck: I bought it to give to her. I've been keeping hold of it ever since. When really what I should do is just return it.

Chuck: How can you be so sure I'm hiding something?
Dr. Barnes: Maybe I'm wrong, but I feel there's a piece of the puzzle still missing. It's not your mother or your father. It's someone you're not telling me about.

Chuck: The dream starts the same every time.
Dr. Barnes: They have a habit of doing that.

Dr. Eliza Barnes: So how are you feeling today?
Chuck: Fit as a fiddle.

Nate: What are you going to do?
Chuck: Take an interest in what matters to Dr. Barnes. Shalom.

Dr. Eliza Barnes: It's obvious that you're deeply troubled and I would be more than happy to help if you were truly interested—in therapy. Now if you'll excuse me, I have Yom Kippur services.
Chuck: Oh. You're Jewish.
Dr. Eliza Barnes: Not that that's any of your business, but I converted.
Chuck: Well that's probably a smart move in your line of work.

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.