Serena: You gonna be okay alone?
Blair: Not yet. But I need to start learning to be. Go have fun with your parolee.
[S gets a text]
Serena: Maybe it's a secret Valentine.

Blair: Well. They're not Richart, but they're all I could find at this hour. I was going to leave them on your pillow.
Serena: Blair, please. It's been a long night. I'm tired.
Blair: You were right. Chuck and Reina are real. Were real anyway.

Serena: Blair. I can't believe you ambushed me. And why? For a leg up at work? Is your career really more important than our friendship.
Blair: Obviously you don't think my career is important at all, since you forced Reina to back out just so you didn't have to be alone on Valentine's Day.
Serena: That's not why I did it. I had a good reason.
Blair: You can't stand that I'm getting successful while you're flailing around with 15 hours of class and an ex-con.

Blair still has feelings for Chuck so... if she follows you around on Valentine's Day she's gonna be hurt. And if she finds out I ever told you this, I'm gonna be hurt.

Serena: So you sound pretty excited about tomorrow. Loke maybe it's not just another night of hanging out with Chuck, business-as-usual.
Raina: I guess that's true. At first it was purely for the sex.
Serena: That's Chuck.
Raina: No, I meant me.

Serena: Blair has to follow a socialite around on Valentine's Day. It's for work. She figured you wouldn't mind since everything with Raina is... you know.
Chuck: "I know," what?
Serena: Oh. Blair was wrong. You do have feelings for Raina.

Blair: Because I need to do a story on Raina for the magazine tomorrow night.
Serena: Okay, well why don't you just ask her yourself. After the Chuck thing doesn't she owe you a favor?
Blair: Yes, but she's not answering her phone and I can't leave the office. Besides it's better this way. Just two It Girls talking. Explain that you'll do the profile yourself.
Serena: Right. Because this is all just a favor to me and not a convoluted way for you to keep your eye on Raina and Chuck during Valentine's Day?
Blair: Hmm. I hadn't thought of that. Thank you!

Blair: How well do you know Raina Thorpe?
Serena: Um, not at all.
Blair: Do you know where she is right now?
Serena: I'm guessing you do.
Blair: At your house.
Serena: Where my mother lives.

Blair: And what about you and Ben? It must be very special for him spending Valentine's Day with someone other than his cellie.
Serena: We decided to sit it out too. We just started dating. It's too much pressure. Hey, why don't you and I have a Friends Valentine's Day? Manis, macaroons, massages?

Serena: I thought you reached out to Raina and told her that Chuck's feelings were real.
Blair: He needed to get back in her good graces and I knew exactly how to get him there. Chuck and I may some need time to forge our own paths before we risk a romantic rejoining, but we're still there for each other.

Serena: Are you sure you're not just burying yourself in work to avoid thinking about tomorrow?
Blair: Tomorrow? I don't even know what day today is. Last year, Chuck and I honored Valentine's Day by staging our very own Bacchanal. And no, there were no goats, if that's the look that just fluttered across your face.

Serena: Please don't tell me you're leaving already. Between classes at Columbia, your job at W, the only proof that I have you still exist is the faint trace of Chanel in the morning.
Blair: I am so sorry, S. But if I can turn this into a permanent job it'll knock six months off my two-year plan.

Gossip Girl Quotes

Even Blair Waldorf can not bend DNA to her will.

Dan

Hazel: Do you know what you're doing, Little J?
Jenny: I'm not Little J anymore.