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.

Gossip Girl

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

An evening of friends and kugel is just what we need.

Lily

Nate: What are you going to do?
Chuck: Take an interest in what matters to Dr. Barnes. Shalom.

Yes. If everyone else is moving on with their lives then I'm ready to do the same. All the way to Monaco. You're my family now, Louis. And I want to be yours. Tell your mother that I'm going to be a Grimaldi and I intend to live like one.

Blair

Blair: I have an idea for you: quit. Your boss is a bitch. Let's go to lunch.
Serena: My job is important to me, B. You have six months to deal with your problem. I have six minutes to deal with mine. Goodbye.

Gossip Girl Season 5 Episode 5 Quotes

Blair: I hope they take it well. Nothing matters more than our child being born into a big happy family.
Louis: Are you ready?

On the Upper East Side, it's not what you say that determines who you are. It's what you do.

Gossip Girl