Rufus: At least you don't have to worry about sun damage and we don't have to spend the month of August with Eleanor and Cyrus on that cruise like they suggested. Can you imagine?
Blair: I don't think the Principality of Monaco's yacht counts as a cruise, Mr. Humphrey.

Nate: What are your plans for the summer, Mrs. Humphrey?
Lily: Well I'm going to be getting very pale. This thing doesn't come off until the fall. Just in time to send my baby off to college.
Eric: Sarah Lawrence is like 15 minutes. I don't really think I need to be sent off. A light breeze could take me there.

Rufus: He's getting 20 years.
Chuck: Sounds fair. That's how long he kept the secret.
Lily: Well I wouldn't want to be in his shoes, I'll tell you that.

Blair: It's taking all the power I have to walk away from you.
Chuck: I know. But I need to let you go. You need to let go.
Blair: I'll always love you.
Chuck: I will always love you.

Blair: I didn't want to let you go just yet.
Chuck: Don't let anyone tell you you're not powerful. You're the most powerful woman I know.

Chuck: There's a difference between a great love and the right love. I left the Empire State Building last year after two minutes when you didn't show. Louis waited all night. This is your chance at happiness. You think you shouldn't want it 'cause you've never had it and it scares you. But you deserve your fairytale.
Blair: We make our own fairytales.
Chuck: Only when we have to.

Blair: Why did you just do that?
Chuck: Because of what you said earlier.
Blair: About being happy? Chuck, that's not the most important thing. People don't write sonnets about being compatible. Or novels about shared life goals and stimulating conversation. The great loves are the crazy ones. L'amour fou.
Chuck: Blair we're not living in Paris in the 20s.

Georgina: Did you find that open window?
Charlie: Yeah. But I shouldn't have been looking for it anyways. I, um, was just off my meds.
Georgina: No, I don't think so. I don't think you were ever on meds.

Dan: Hey, what are you doing up here?
Nate: Meeting Serena. You too?
Dan: Why do I feel like we've been here before.

Chuck: The party's almost over.
Louis: I know. But Blair hasn't arrived yet.
Chuck: How could you be sure she's coming?
Louis: Because I love her. And just as important, I believe in her. I know she's scared, but she'll figure it out. And I'll be here when does.

All night I've realized... I didn't choose college. I never chose between Dan and Nate. I didn't even choose paris last year. Blair told me I was going. Trust me, I know what it feels like when you're not making your own decisions.

Serena

Chuck: You really love him, don't you?
Blair: Yes. But not like I love you. Louis and I, it's different. It's lighter, more simple. He makes me happy.
Chuck: And I don't?
Blair: What we have is a great love. It's complicated. Intense. All-consuming. No matter what we do and how much we fight, it'll always pull us in. What's mere happiness in the face of all that, right?

Gossip Girl Season 4 Quotes

Serena: So what does it say about Chuck?
Blair: I couldn't be less interested. Serena gives her a look. No new posts. He's been MIA since he left town this spring.
Serena: What does it say about us?
Blair: "Ooh la la! Paris is burning and Serena and Blair lit the match." Of course your flame is hotter than mine. Everyone knows that the only guy who's been in my pants all summer is the tailor at Pierre Balmain.
Serena: And whose fault is that? B, just as many guys have flirted with you. I just happen to have a thing for French waiters.
Blair: And bartenders. And museum docents. Anyone on a Vespa or bicycle. Or wearing Zadig & Voltaire.

Serena: Blair what are you doing? We said we wouldn't check Gossip Girl all summer.
Blair: Summer's almost over.