Chuck Bass Relationships


Georgina Sparks

He lost his virginity to her in 6th grade.

Blair Waldorf

First Relationship:
Start Up: "Victor, Victrola" (107)
Broke Up: "Hi, Society" (110)
Reason: Chuck jealously ruins Blair's debut ball, leading Blair to reconcile with Nate.

Second Relationship:
Start: "Much "I Do" About Nothing" (118)
Broke Up: Before Summer, Kind of Wonderful (201)
Reason: Chuck was afraid of letting Blair get too close and abandons her at an airport.

Third Relationship:
Start: "The Goodbye Gossip Girl" (225)


Elle
(fling)

Start: Carrnal Knowledge (217)
Broke Up: The Grandfather (219)
Reason: Elle was using Chuck for the money

Jenny Humphrey
(forced)
Start: Pilot (101)

Vanessa Abrams

One Night Stand: Remains of the J (220)
Reason: They both felt alone and betrayed.


Also countless unknown conquests.