GG: On the Upper East Side it’s easy to think the world is exactly as it appears. Refined. Elegant. Imposing. But sometimes all it takes is a little key to open the door to the wild side.
Blair: Good catching up.
Blair: Enough with the blackmail. Aren’t you bored already? I can’t avoid Nate forever.
Chuck: Excuse me. I didn’t say “forever”. Just until the sight of the two of you together doesn’t turn my stomach.
Blair: And when would that be?
Chuck: Only time will tell, I’m afraid. So unless you want dear Nathaniel to know how you lost your virginity to me in the back of a moving vehicle, I encourage patience and restraint.
Blair: Isn’t there someone else you could torture?
Chuck: Probably. But I choose you.
Vanessa (Jessica Szohr): Come on! Be interesting. You don’t want me to move back to Vermont, do you?
Dan: No. But if your whole future depends on you getting this grant for your documentary I really really think you should find a new subject.
Vanessa: Absolutely not. “The outsider goes inside: A likeable everyman’s pursuit of his dream girl begins his descent into the bowels of Hell.” This is mythic stuff.
Vanessa: So what will it be, Dan? Cheerios and Chaucer or an illegal party at your prep school with your high society girlfriend and her nasty cohorts?
Dan: Dad? Vanessa and I are going out.
Dan: Well if you wanted to get the perfect shot of me feeling like an outsider I’m ready for my close up.
Headmistress Queller (Linda Emond): Ten thousand words describing how you came to be on school property after hours using alcohol and drugs where a fellow student almost died. In other words, what the hell is wrong with you?
Blair: So we all know how this works.
Chuck: No one talks, no one gets into trouble.
Nate: Who did break in, anyway?
Chuck: Guess we don’t have to worry about Nate cracking under pressure.
Blair: So are we all agreed?
Dan: Look Blair, I know you had your sights set on Yale but this Skull and Bones thing is a little much, don’t you think?
Blair: Maybe. But it works. Every time.
Gossip Girl: There’s a weak link in every chain. And it’s just a matter of time before this one snaps.
Headmistress Queller: I reviewed your record. It’s pristine. If Constance had a shining star, it’s Blair Waldorf. I would never have expected this from you.
Blair: I know. I’m the perfect one.
Chuck: You’re taking the paper seriously.
Nate: This isn’t the paper, it’s a heartfelt letter to Blair.
Chuck: A heartfelt letter? Who spayed you, man? Blair doesn’t even want you. She’s been crystal about that since we got back.
Nate: Didn’t seem that way when she kissed me in the pool.
Rufus: Don’t think for a second these other kids aren’t going to be looking out for themselves. You should do the same. Alright?
Lily: I hope I’m not interrupting anything. I just got a message that our kids are in some kind of trouble at school.
Rufus: And you came all the way to Brooklyn to talk about it?
Lily: No no, not about that. Bart and I just landed at the airport back from our trip. And he proposed. And I’m going to say yes. I wanted you to hear it from me first. Not from my daughter or your son.
Rufus: Right. People who actually talk to me.
Lily: Oh, if you’re referring to the message you left me on Christmas Day I didn’t get it ’til we were already on the plane. It was… very endearing though.
Rufus: But not enough to turn a G5 around.
Lily: You miss me. That’s great. I miss you too. What? You kissed me at Eleanor’s party and then you say you can’t see me anymore because your wife came home. And then you call and say you should have never let me go. And then you’re back with Allison again.
Rufus: I didn’t plan any of that.
Lily: That’s just it, Rufus. You don’t plan anything.
Rufus: Well, I’m sure that your current plan will be full of jets and five-star hotels.
Lily: Take care, Rufus.
Gossip Girl: Spotted: Lonely Boy learning that when the punishment fits the crime there is no reason you can’t serve your sentence in style.
Blair: You are so naive. Michael Moore over there is obviously just using this film to get close to Dan.
Chuck to Dan: In case you’re wondering, narc, I only took that key from the party to hide it that we wouldn’t all get blamed. Including you.
Dan to Serena: Maybe the reason none of you guys take it seriously is because for you, it’s not.
Rufus: Why did you really come to see me yesterday?
Lily: I told you, out of respect—
Rufus: Respect or regret? You wanted me to give you a reason not to spend the rest of your life with Bart Bass.
Rufus: I’m still in love with you.
Rufus: Claim your life this time. Live it the way you want to live it.
Headmistress Queller to Nate: From what I can see, you always seem to be toting the line of mediocrity.
Vanessa: What are you going to do to me, Blair? Blackball me from eating yogurt on the Met steps?
Vanessa: What’s that? Your stripper money?
Dan: Wow. You really can be damned if you do and screwed if you don’t.
Serena: I would rather be Chuck’s stepsister than Dan’s.
Vanessa: I know this may come as a shock. But not everyone operates from an agenda. In fact some people do things simply because it’s the decent thing to do. Smash it, burn, whatever. There are no copies.
Blair: What about the one you gave to Chuck?
Vanessa: It’s blank. Which I’m sure he will be thrilled to discover. And having observed you in your natural habitat these last few days, Nate seems like one of the good guys. And you seem to really care about him.
Headmistress Queller: Who had the key to the school?
Dan: I don’t know.
Headmistress Queller: Let me remind you that you are in a different position from the others. You need this school.
Vanessa: You talked to my landlord?
Blair: I don’t speak Ukrainian.
Dan: You going to Brooklyn?