Chuck: I'm sorry. I screwed up.
Blair: It's too late, Chuck. I stood by you through all of this but I can't watch you self-destruct any longer.

Dan: Through all this I had so many thoughts going through my head, but the one that kept popping up again and again: what does this mean—for us?
Serena: I don't know, but we'll figure it out. Because I know no matter what I want to be with you.
Dan: Me too.

Serena: I don't know. I had enough trouble with the idea of mom and Rufus dating, but now I share a sibling with my boyfriend. That's little more hillbilly than I can handle.
Eric: It is a little twisted. But so what?
Serena: Well what if we can't get past it?
Eric: I don't know. But you can't push Dan away right now. Whatever you are going through he's going through the same thing.

Chuck: You're my only family. How could you do this to me?
Jack: You did it to yourself. Clearly I was right and you weren't ready.

I don't need your help. Stop trying to play the wife.

Chuck

They don't want to meet. They don't want us to contact them. Ever.

Rufus

Blair: (reading the letter) Dear Son, I know I've always been hard on you—
Chuck: True.
Blair: —but my goal was always to prepare you for this day. To help you go from being a boy to a man.
Chuck: An Italian au pere took care of that.
Blair: Chuck, please. Sadly, there is nothing like the passing of a father to aid in this rite of passage for his son. Ultimately I do feel that I did my job and you are prepared for this next chapter of your life. Therefore I am bequeathing to you the majority share of Bass Industries.
Chuck: Surely that's a mistake.

Jack: Come out with me tonight.
Blair: I told you I'm not interested.
Jack: Didn't seem that way on New Years.
Blair: Whatever may have transpired between us, what's important is what it means to me. Which is nothing.

Blair: Morning Jack.
Jack: Blair.
Blair: Chuck asked me to come to the reading of the will for support.
Jack: Only thing he's going to need support for is the massive influx into his bank account.
Blair: Charming.

I don't want to spend another day yet another minute trapped in this hotel room scared that you are going to hate me forever... when I'm still in love with you.

Lily

Lawyer: Are you comfortable with this?
Chuck: Curfew?
Jack: None.
Chuck: Girls sleeping over?
Jack: Yes, please.
Chuck: I'll allow it.

Jack: Why would he leave Bass Industries to you, a teenager who can't his pecker in his pants for more than 24 hours.
Chuck: At least I can keep it in service for more than five minutes.

Gossip Girl Season 2 Episode 15 Quotes

Nelly: We should at least tell Blair.
Isabel: We can't. Blair's with Chuck. Again.
Penelope: I'm really getting sick of how much time she's spending with him.
Isabel: His dad just died.
Penelope: Yeah, like a month ago.

Serena: Look, I know you've been avoiding me, but my mom called from Boston this morning and I asked her point blank. You have nothing to worry about.
Dan: Worried? Who said anything about being worried? What'd she say?
Serena: That there's nothing going on between her and Rufus.
Dan ... Oh.