Chuck: I had it all wrong. Just because Louis is the father of your baby does not mean you should be with him, you should be with me.
Blair: Why?
Chuck: Because I'm going to love your baby as much as I love you.

Blair: Why did you tell me to choose Louis?
Chuck: I thought it was selfish if I was the one to tell you to break up your family.
Blair: That was the moment you chose not to be selfish?

Gossip Girl: Sorry, boys. But didn't you know that if you wait to long to seize the day—
Chuck: Gone.
Louis: Where would she go?
Gossip Girl: The one you want could get away.

Louis: What are you doing here?
Chuck: Apparently the same as you. The Prince and the Pill-popper. This should be fun.

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.

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.

Chuck: You should know better than anyone, these stories are invented to sell papers to women who collect ceramic cats.
Nate: Still, maybe you should give her a call.
Chuck: Louis is the father of her child. There's no way Blair's walking away from that.

So you're finally learning there are upsides to pissing off your family.

Nate: So I don't get it, you kissed Blair so she'd think you hadn't changed?
Chuck: The only way for Blair to move on is if she thinks I never will. I had to kiss her to set her free.
Nate: That may be the most selfless thing you've ever done.
Chuck: I've never been more good and less happy about it.

Blair: Do you remember when we used to play dress-up?
Chuck: How could I forget. Though I didn't think this was your kind of entertainment anymore.

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.