Serena van der Woodsen (forced)
Donetella Contessa (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)
Start: Victor, Victrola (107)
Broke Up: Hi, Society! (110)
Reason: Blair believed that Chuck purposely ruined her Cotillion.
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.