Chuck Bass Relationships
He lost his virginity to her in 6th grade.
Start Up: "Victor, Victrola" (107)
Broke Up: "Hi, Society" (110)
Reason: Chuck jealously ruins Blair's debut ball, leading Blair to reconcile with Nate.
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.
Start: "The Goodbye Gossip Girl" (225)
Start: Carrnal Knowledge (217)
Broke Up: The Grandfather (219)
Reason: Elle was using Chuck for the money
Start: Pilot (101)
One Night Stand: Remains of the J (220)
Reason: They both felt alone and betrayed.
Also countless unknown conquests.