1. Summer, Kind of Wonderful

Blair: The only thing lamer than dating Dan Humphrey... is mourning Dan Humphrey.

Blair: Damn that mother Chucker! He's totally right! I don't even like James!

Blair: Chuck is an awful person. He does awful things.

Blair: The true reason I should stay right where I am and not get in the car. Three words. Eight letters. Say it and I'm yours.

Blair: A hot lifeguard is like kleenex! Use once and throw away. toi could ask for a better rebound!

Blair: I wasn't aware that robots got jealous. Did they update your software while I was away?

Blair: Oh, a honk instead of a knock!...

Blair Waldorf Relationships

Nate Archibald

First Relationship:
Start Up: Before "Pilot" (1.01)
Broke Up: "Victor, Victrola" (1.07)
Reason: Blair confronts Nate about his confession to 'Serena'.

Second Relationship:
Start Up: "Hi, Society" (1.10)
Broke Up: "School Lies" (1.12)
Reason: Chuck threatens to tell Nate about his and Blair's relationship if she continues seeing him.

Third Relationship:
Start Up: "School Lies" (1.12)
Broke Up: "A Thin Line Between Chuck and Nate" (1.13)
Reason: Nate finds out that Blair slept with Chuck.

Fourth Relationship:
Start Up: Remains of the J (2.20)
Broke Up: Seder Anything...