Serena: Woah. Usually when you smile like this you look like a creepy Cheshire Cat. But this one is real. What is your secret and if it's legal I want some.
Chuck: It's not a substance. It's a state of mind. A word.
Serena: Let me guess, a dirty word.
Chuck: "Yes".

Serena: How did you guys end up here? And who's boat is this?
Nate: This is Allegra Versace's. Chuck won it in a poker game in Chiang Mai. He won Allegra too, but that's another story.

Blair: How did you know just what I was missing. Shall I wear it to your uncle's speech at the General Assembly tomorrow?
Louis: Unfortunately you will not be allowed inside until you are an official member of the royal family. Consider yourself lucky. [?] speeches are stronger than Ambien.

Louis: How does it feel to be home?
Blair: Oh, it's going to be tough reacclimating after living in a palace. How will the penthouse do? But maybe we should skip the wedding planning and pull the blinds and just spend the day in bed.
Louis: We did that all summer. But we can't put off our parents any longer. Would a present help motivate you downstairs?

Chuck: Anything for me?
Nate: Nope.
Chuck: Well if you hear anything crazy it means I'm doing something right.

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.

Gossip Girl Season 5 Quotes

Chuck: I'm sorry for losing my temper the night you told me Louis proposed to you. I'm sorry for not waiting longer at the Empire State Building. I'm sorry for treating you like property. I'm sorry I didn't tell you I loved you when I knew I did. Most of all I'm sorry I gave up on us when you never did.
Blair: Thank you.

They say every road comes to an end, but sometimes the end feels just like the beginning. Even when you think you've come a long way, you can suddenly find yourself right back where you started. Because every journey is fraught with twists and turns.

Gossip Girl