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.

It's cold out there, but on the Upper East Side things are heating up. Because Valentine's Day is around the corner.

Gossip Girl: Looks like our favourite Upper-East sinners just find the answer to their prayers.
Chuck & Blair: I need your help.
Gossip Girl: Lucky for us their road to heaven leads straight through hell.

One lonely Bass adrift at sea.

Roses are red, hydrangeas are blue. Chuck's given his heart away ... But guess what, Blair? Not to you.

This experience taught me one thing. I still got game.

The Captain

Wall Street didn't need a sequel. In theaters, or in my life.

The Captain

[to Serena] It's okay to date below the line. Madonna and Julia Roberts paved the way for girls like you.

Blair

Thank you for saving me from a Valentine's Day even more depressing than the movie I was going to watch about it.

Serena

Gossip Girl Season 4 Quotes

Serena: Did you just get a key?
Girl: Yep. And my mom said I'd never get in unless I lost 10 pounds. She's a bitch.

Chuck: You don't have to be powerful on your own first. We can build our futures together.
Blair: The saddest part is that I'd come to the same conclusion. But now that I know I'm ready I realize you're not. I mean, after everything you went through—Prague, Eva, Russell—that maybe you'd changed. Who was kidding.
Chuck: Don't say that.
Blair: You have years before you're capable of a real relationship. If you ever will be. I'm sorry Chuck.