(to Rachel) Well, the Headmistress told me my fate at Yale is sealed. So the question is, how do I make your fate as bleak as mine?

Blair

Serena: Everything you've done, spreading rumors about who I've had sex with, what alley I puked in or telling Dean Barrowby that I killed Pete Fairman, I forgave everything all because I thought one day you'd grow up. But putting up a Gossip Girl blast about Yale and the press release ...
Blair: Serena, I didn't put out the blast.
Serena: At least have the dignity not to lie to my face.
Blair: But I'm not lying.
Serena: Only two people knew about it, you and Dan. And Dan would never do something like that. I always want to believe the best in you, Blair, but the bottom line is, betrayal's in your nature.

Blair: Everyone's jealous of me, because my life is perfect and you've always been the most jealous of all.
Nelly: People aren't jealous of you, Blair. They hate you.

Poor Miss Iowa caught playing Mrs Robinson. Looks like the teacher just got schooled.

Nelly: What is your problem?
Blair: My problem is a two-faced, four-eyed, devious little snipe in a fat-suit. Did you really think you could rat me out to Yale and get away with it?

Vanessa: Serena, I know you like him, but as your friend, Julian is the most self-absorbed pompous person I have ever met. All he does is go on and on about classic movies and it's totally annoying.
Serena: You were keeping up with him pretty good there.
Vanessa: Yeah. And I'm totally annoying.

In life, as in art, some endings are bittersweet. Especially when it comes to love. Sometimes fate throws two lovers together only to rip them apart. Sometimes the hero finally makes the right choice but the timing is all wrong. And, as they say, timing is everything. Looks like this story might just have a second act. Let's hope it's not a tragedy. XOXO. Gossip Girl.

Serena: You know, I don't know why I ever had a crush on you.
Julian: Serena, I'm gay.

Blair: The head mistress told me my Yale at fate is sealed, so the question is - how do I make your fate as bleak as mine?
Rachel: I don't know what has happened to me. I... I don't know what I've become. I'm... so sorry.
Blair: Well, you're punishment is... just live with it. I should know. It's not easy.

Sometimes, the hero finally makes the right choice, but the timing is all wrong.

Carter: Hello, beautiful.
Blair: Carter, what are you doing here?
Carter: Buying you a drink.

Welcome to the next 30 years.

Tripp

Gossip Girl Season 2 Quotes

Serena: Blair will never forgive you for what you did to her.
Chuck: Who told you that little piece of advice, your boyfriend Nate?
Serena: Nate didn't say anything ...
Chuck: Good. I don't think it's wise taking relationship advice from someone in a FAKE relationship. Call me crazy. (pause) Enjoy another night alone with your thoughts.
Serena: Good luck on your suicide mission!

Serena: I still miss Dan sometimes... more than sometimes.
Blair: The only thing lamer than dating Dan Humphrey... is mourning Dan Humphrey.