I'm vulnerable. He's devastated me, but he's also made me happier than I've ever been. I just don't know which kind of love is better.

Blair

Chuck: You didn't need to buy me a gift.
Bart: Actually you bought it. I was in Harry Winston picking up an apology trinket for Lily. Helene told me it was in the vault. I thought you might want it back.
Chuck: Why?
Bart: Well isn't Blair the most important thing in your life? Where's that last grand gesture we spoke of earlier?
Chuck: Maybe I'll just hold on to it.

You look just as beautiful in black as you did in white.

Serena

Serena: Blair's dirty work can wait.
Penelope: She fired me. I'm on the way to meet everyone at Michael Jordan's Steak House for the Shepherd's divorce party.
Serena: Alright, well there's been a change of plans. You're not going to that. And neither is Blair. And you and your friends are going to see to it.
Gossip Girl: That's the problem with hired help. They'll work for anyone.

Chuck: What are you doing here?
Blair: I came to check on you. Gossip Girl's been putting a bunch of stuff up and I wanted to make sure that you weren't hurt—
Chuck: Why would I be hurt about something that was in your diary a year ago? We've been through so much since then. talked about everything, made amends. Or is there some other reason you're here? Maybe to tell me you and Dan broke up?
Blair: No. We haven't.
Chuck: I can't play this game anymore, Blair. I spent a whole year waiting for you. I need to move forward.
Blair: No, you're right.

Bart: I am proud of you, son. Lily told me you stepped up but I had no idea how much you'd accomplished.
Chuck: Thank you. How was seeing Lily after all this time?
Bart: I never dealt with such a formidable woman. Made me regret not treating her better.
Chuck: They require dedication.
Bart: I assume you're talking about Blair Waldorf. But you two aren't back together?
Chuck: I made a lot of mistakes after you left. I lost my temper. I lost myself. When I finally realized what I'd done and I had the ring to propose it was too late.

Go move in with Nate. Don't turn your back on the life that I almost screwed up for you.

Lola

Carol: Well it's about time William gave you my money. I was starting to worry he'd made some secret alliance with Lily.
Lola: I guess it just took awhile to arrange everything.

Blair: "I'll never love Chuck again after what he did tonight. He's a monster. He deserves to be alone forever." I was waiting for that one. You happy now? Now that I'm as alone as you are?
Serena: I'm only alone because of you. You had your prince and you had Chuck. You didn't need to take Dan too.
Blair: I didn't take Dan. That's not how relationships work. You would know that if you'd grown up at all since high school.
Serena: Oh come on, Blair. You're the one that can't move on. You're still in love with Chuck and you still won't admit it.
Blair: Get out! I mean it. I want you gone for good. Pack your things.
Serena: You can't hold me responsible for everything bad in your life.
Blair: I can. Because you are. The best time I ever had was when you were gone six years ago. Leave your key with Dorota.

Serena: You knew how important that job was to me. And I was on the verge of getting another one.
Blair: Summer job on a film set versus exposing all my secrets. No, I'm not sorry.

Bart: Rufus. You're looking well. I see your transition from Brooklyn to the big time has done you wonders.
Rufus: I'm not here for small talk. I just need you to sign these annulment papers.
Bart: So. Lily has chosen to end our marriage in order to save yours.
Rufus: She made her choice three years ago when she decided to leave you for me. Nothing's changed since then.
Bart: Maybe I have. All that time in hiding made me realize what's really important.
Rufus: What does that mean exactly?
Bart: If Lily's happiness depends on my signature on these, you will have them by the end of the day.

Dan: Blair I told you I loved you and you pretended like you didn't even hear me.
Blair: Dan, let's just put all that behind us.
Dan: See, you're doing it again. Do you even want to be in this relationship?
Blair: Of course!
Dan: Is the reason you can't say you love me because you're still in love with Chuck?
Blair: No.
Dan: Then I need to know how you feel about me. By tonight.
Blair: Dan—
Dan: We're supposed to be spending the summer in Italy together and I don't want you coming unless we know where we stand.

Gossip Girl Season 5 Quotes

Even Blair Waldorf can not bend DNA to her will.

Dan

Dan: Do you really want to spend the entire summer with me in Rome? Chuck's dad is alive. That is going to change his world deeply.
Blair: His, yes. But not mine.