Devastated by the recent plot twist in her life, Blair turns her back on her predictable Waldorf existence in favor of a more wild and unpredictable lifestyle, causing Serena and Chuck to have serious concerns about their friend. Vanessa convinces Nate that it may be time to forgive and forget when it comes to his mother's Kennedyesque family, The van der Bilts, who abandoned Nate and his mother when they needed them most. In a misguided effort to be completely honest with each other, Lily and Rufus agree to share lists of their past lovers.
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Chuck: I would have come here earlier. I stopped to pick up something.
Blair: How thoughtful.
Chuck: Serena thinks you're in some kind of trouble. Seems to me your only problem is having a party all by your lonesome.
Carter: Except she's not alone.
Chuck: What are you doing with this insect?
Blair: Having the time of my life. Thank you very much.
Chuck: Well as much as I enjoy bursting your bubble, he's just using you to get at me. Ask him about his role as a kidnapper for a certain secret gentleman's club. I should know, I had him expelled.
Carter: Oh please. All I did is bring that girl to a waiting pile of cash. Which I understand she gladly took before leaving town. Without you.
Chuck: Blair. This guy—
Blair: What? Dishonest? Bad news? He can't be any worse than you.
Chuck: I'm the one trying to help you!
Blair: Help me? Is that what you were doing at your little gentleman's club while my life was going up in flames? I'd rather take Carter's help.
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Serena: Hey. We have a problem.
Chuck: Let me guess. Carter Baizen. As usual you're a step behind.
Serena: He's encouraging the worst in her.
Chuck: True. Unfortunately my PI has yet to dig up an unpaid creditor or a jealous husband that would clear Baizen out.
Serena: Tell him you want to see him.
Chuck: Why? What do you have?
Serena: Just do it.
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Carter: I'm surprised. You waved the white flag so soon. He drains his drink. Goes down almost as easy as you did.
Chuck: So it was all just a game?
Carter: Initially, yes. Though I have to admit Blair surprised me. That girl certainly knows how to let loose. Victory never tasted so sweet. Speaking of which, do you mind if I take this? Blair's meeting me at a party and it's not the kind of place she should be left alone.
Serena: Actually I don't think you're going to be making that.
Carter: What's this? Good cop, Bass cop?
Serena: Blair needs to regroup so you need to bid adieu.
Carter: Dubai again. Nice try but I'm having too much fun. Nothing's going to get me to leave town.
Serena: What about Santorini? You think Blair will want to hear about that? The Greek guy Spiros? The Greek police. I still have all their phone numbers from when they questioned me.
Carter: You wouldn't.
Serena: I would. But I won't if you leave town now. Alone.
Carter: There are a few things I could hold over your head from that trip. But consider us even. If the two of you think that getting rid of me is going to magically change back your friend, think again. I'm just a symptom of the disease. Not the cause.
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Society Matron: Blair Waldorf. How are you, dear? I heard you rejected The Colony Club. Too stuffy for my tastes as well.
Blair: That's because your tastes include sleeping with your driver and popping prescription mends.
Serena: Okay. Not good.
Blair: Not good. Like Dan having sex with Rachel Carr in the costume closet during the school play not good. By the end of tonight the old Blair will be dead and buried with no chance for a resurrection. Hey! You! Garçon with the bubble butt. Arrête.
Serena: Well. That was...
Chuck: Go find Dan. I'll make sure this social eulogy doesn't get out of hand.
Serena: Thanks Chuck.
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Chuck: What are you doing? Trying to destroy the old you? Burn every bridge? It won't help. Believe me, I've tried.
Blair: Well maybe I should head up to the roof, make it a little more dramatic.
Chuck: This isn't you.
Blair: How would you know?
Chuck: Because I know you better than I know myself.
Blair: Oh. Right. You can see right through me. Can't you, Chuck? Right to my core. Do you remember the first time you saw the real me? The Blair that danced for you that night at Victrola? The Blair with none of the hangups, none of the frustrations. That's the Blair right here. Take me now.
Chuck: Why?
Blair: To prove that nothing matters.
Chuck: No. This isn't you. It's not the Blair I want.
Blair: That's right. And I never will be again.
Gossip Girl: The danger with calling someone's bluff is that even if you win—
Blair: Goodbye Chuck.
Gossip Girl: —you risk them walking away from the table for good. And who wants to play with themselves?
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Serena: Chuck. No reaction. Okay, fine. Have fun drinking by yourself. She turns to leave.
Chuck: I'm losing her.
Serena: Well then fight for her. She did for you.
Chuck: I tried. And failed.
Serena: Well then try again, Chuck. Her plan didn't work out for her and she doesn't know what's going to happen next. If you want to be back in her life make her feel safe. You know what to say.
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Dorota: I told doorman, no visitors. Mr. Chuck. It's late.
Chuck: I just need a moment of her time.
Dorota: Miss Blair asleep. I'm sorry.
Chuck: Can you tell her that I stopped by and that I have something I need to tell her?
Dorota: I will. In morning.
discovering that your best friend just won over the girl you love
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