Charlie: And thanks again for helping me do nothing.
Nate: Well it was fun breaking into the safe.

That's the thing about writing what you know. Soon everybody else knows it too.

Serena: I finally finished the book.
Dan: I told you, it's not you. Yes, there are parts of you. And Daisy Buchanan. And Amy March. And Gwyneth Paltrow. Five different roles she's played. But it's a novel. It's inspired by a lot of things. It isn't speaking to some deeper truth.
Serena: Are you sure? Because I know this may sound crazy or selfish or... like I'm living in the past or something. But you were the love of my life, Dan. I don't know, I just thought I was yours too.

Serena: I followed Jane all the way done to her town car apologizing, and even then I don't think it was enough. Thank you for waiting.
Dan: I didn't want to. You scared away everyone, and now no one wants the book.
Serena: Dan—
Dan: Your apology this morning was just strategic, wasn't it?
Serena: Yeah. Pretty much.

You asked for my professional opinion and now you're going to get it. You never had a childhood and now you behave like a child in the worst ways. You pay for intimacy so you're always in control and no one can get close to you. Your superficial connections and lack of authentic emotion leave you isolated and alone. Not just tonight. Always. I wish you all the best, but you're going to need more than that to live a happy and normal life.

Dr. Eliza Barnes

These might be my friends but they're your family. And you're acting like you barely know them.

Nate

Charlie: This is the mother lode. The biggest secrets of the Upper East Side. Even one of these would not only launch the web site but blow Diana's mind.
Nate: And my ethics. These are my friends. Now that I've actually done this, I don't know what I was thinking.

Sophie: The clause stays. If you two cannot accept this, then I will not acknowledge the child as my heir. Nor will I acknowledge you.
Louis: You don't have that right anymore. As the future reigning prince, it's up to my child to acknowledge you.

Cyrus: And furthermore it says that if you break any of these rules you face the possibility of losing custody of your child to the royal family.
Blair: What? Wait, that's—
Louis: Outrageous.

Rufus: Since I'm feeling a little raw on the family front, if Eleanor refers to you as Lily Bass again I can't promise I won't return fire.
Lily: I dragged you here, and you have my full blessing to go Sean Penn if need be.

Sometimes all it takes to cross a line is a little push.

Maybe your good friend F. Scott Fitzjackass had you nailed in the book. If something doesn't fall right into your lap, Serena, you don't have a clue how to work for it.

Jane

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.