Leighton and Chace in Toronto

Flings and romantic relationships

Book Series
Nate Archibald (lovers/dated)
Miles (fling)
Owen Wells (fling)
Lord Marcus Beaton-Rhodes (dated)
Jason (fling)
Erik van der Woodsen (fling)

TV Series
Nate Archibald
First Relationship:
Start Up: Before Pilot (101)
Broke Up: Victor, Victrola (107)
Reason: Blair doesn't feel that Nate loves her anymore, and he refuses to confide in her about his dad's drug problem and abuse. Not to mention the fact that he confessed feelings for and kissed "Serena" at the masquerade ball.
Second Relationship:
Start Up: Hi Society (110)
Broke Up: School Lies (112)
Reason:...