Book Series
Serena van der Woodsen (forced)
Donetella Contessa (fling)
Tiphany (fling)
Jenny Humphrey (forced)
Kati Farkas (fling)
Katie Soave (fling)
Katherina Esmée Guaraná-Bianchini (ex girlfriend)
Georgina Sparks (fling)
All Male-Dutch Snowboarding team (fling)
Greg (boyfriend)
TV Series
Blair Waldorf
First Relationship:
Start: Victor, Victrola (107)
Broke Up: Hi, Society! (110)
Reason: Blair believed that Chuck purposely ruined her Cotillion.
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.
Serena van der Woodsen (forced)
Donetella Contessa (fling)
Tiphany (fling)
Jenny Humphrey (forced)
Kati Farkas (fling)
Katie Soave (fling)
Katherina Esmée Guaraná-Bianchini (ex girlfriend)
Georgina Sparks (fling)
All Male-Dutch Snowboarding team (fling)
Greg (boyfriend)
TV Series
Blair Waldorf
First Relationship:
Start: Victor, Victrola (107)
Broke Up: Hi, Society! (110)
Reason: Blair believed that Chuck purposely ruined her Cotillion.
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.
