Dan: What do you really want?
Blair: To be happy. But I don't think I know how to anymore.
Dan: Well I think I know how to make you happy.

Blair: It's decided.
Dan: Chuck?
Blair: Nope. Apparently there are some risks even Chuck Bass isn't willing to take. So. Problem solved.

Chuck: The idea of unconditional love is as quaint as the Tooth Fairy or environmentally-friendly drycleaning.
Lily: Not when you're a parent. Look you might only be my son by marriage, Charles, but I've always loved you as my own. And I hope you get the opportunity to feel that with someone some day.

Lily: I'm always here for you. No matter how ugly or dark your feelings may be, you should not have to bear them alone.
Chuck: I appreciate it, Lily, but you have no idea what you'd be taking on.
Lily: Are you kidding? Of course I do. Try as you might, you don't scare me. I'm sorry to inform you that my love for you is unconditional.

Nate: My grandfather just admitted to me that the only reason I have this job is because he bought the Spectator. Here I was, thinking I was doing great work and so proud of it, now I just feel like a total fraud.
Charlie: It doesn't matter how you got here, Nate.

They say love is blind. But jealousy it seems provides a clear view all the way to Monaco.

Serena: Telling her your feelings is not going to change your ending, it's just going to mess with hers.
Dan: Well listen, the fact is, this doesn't concern you at all. I'm going to talk to Blair. And even if it's the biggest kami kaze disaster of my life, it's my disaster—it's my ending. So please, stay out of it.

Blair: Do you think you could love another man's child.
Chuck: Why are you asking me this?
Blair: I'm paralyzed. I can't move, I can't breathe. You have to help me.
Chuck: I can't make this decision for you, Blair. You're the one that has to live with it.
Blair: But what's the right choice, Chuck?
Chuck: I can't imagine it would be a mistake to marry to father of your child. Right?

Blair: I need your advice. It seems as you've found your way I've lost mine.
Chuck: I didn't think Blair Waldorf could get lost.
Blair: Neither did I but I'm so lost I wound up in Brooklyn.
Chuck: There are worse places. This isn't something Humphrey can help you with?
Blair: No. Only you.

You know the truth is I don't think I ever got it right before Dan. Or since then. Besides Nate he's probably the only good guy I've ever dated.

Serena

Blair: I'll start with Chuck. Pros: he truly has become a good man.
Dan: Cons: he's slept with every woman in New York. It could get a little awkward at dinner parties.
Blair: Sometimes fun. Don't judge.

Dan: I saw your photo in the paper. Is everything okay?
Blair: Everything is horrible. I need to go to Louis and reassure him that he's never going to lose me but something is stopping me.
Dan: Chuck is stopping you.
Blair: No. I haven't even spoken to Chuck.
Dan: You don't have to. You have some strange force field effect on each other. Physicists should study it.

Gossip Girl Season 5 Quotes

Dan: It's Blair's Save the Date.
Rufus: You're not happy. You guys are still friends, right?
Dan: Yeah. Friends. I wonder if she invited Chuck.
Rufus: If he's anywhere that FedEx can reach.

Dan: Dad! What are you doing here? I thought you'd still be in London helping Jenny set up St. Martin's.
Rufus: She and Eric kicked me out when I didn't know who Sierra Burton was, so I came back here early and thought I'd spend some time with you.