Do you ever get tired of carrying around that chip on your shoulder?

Nate: I thought we were gonna do something. What happened to your master plan of finding the Skull & Bones?
Chuck: You don't find them. They find you.

[to Chuck] Good luck sitting on your ass.

Nate: You crash the party, and tell me to break it off with Catherine. Then you pull a 180 and tell me to stay with her. And then you just bolt. I mean, did I do something? Or... what happened?
Vanessa: I'm late.
Nate: Oh so that's it. We're not even friends now?
Vanessa: We were never really friends, Nate.

Vanessa: Nate? What are you doing here?
Nate: You haven't returned my phone calls.
Vanessa: I've ... been busy.

Nate: Vanessa? I couldn't find her. Vanessa?!
Catherine: [turns on lights] Your friend had to leave. Was there something you wanted to tell me?

Vanessa: I don't believe this. I kept telling myself you were different than Blair and all the others, but you're just as bad!
Nate: It's not that simple, okay?
Vanessa: Are you sleeping with that woman?
Nate: Yes.
Vanessa: Is that the reason you keep canceling on me?
Nate: Yes, but...
Vanessa: No, Nate, there are no buts. You lied to me and you're sleeping with some Mrs. Robinson. And while on the Upper East Side that might be totally normal, I didn't sign up for some love triangle with you and somebody's mom!

[to Vanessa] When you called the other day, it was like... I could breathe again.

Catherine: Ralph Lauren adores you.
Nate: Did you hear what I just said?
Catherine: I did. What happened to the money I gave you?
Nate: It's gone, but I can repay you back as soon as our accounts are unfrozen.
Catherine: Which won't be until your father returns from... where was it? Dominica?
Nate: I told you that in confidence!
Catherine: You told me that in bed.

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