Flings and romantic relationships
Blair Waldorf (on and off girlfriend/lover)
Serena van der Woodsen (ex-lover)
Jenny Humphrey (ex-girlfriend)
Georgina Sparks (ex-girlfriend)
Start Up: Before Pilot (101) (They are said to have been dating since kindergarten.)
Broke Up: Victor, Victrola (107)
Reason: Blair confronts Nate about his confession to 'Serena'.
Start Up: Hi, Society (110)
Broke Up: School Lies (112)
Reason: Chuck threatens to tell Nate about their relationship if Blair continues seeing him.
Start Up: School Lies (112)
Broke Up: The Thin Line Between Chuck and Nate (113)
Reason: Nate learns about Blair's secret relationship with Chuck.
Start Up: Desperately Seeking Serena (115)
Broke Up: Much "I Do" About Nothing (118)
Reason: Nate felt like he had too much going on and needed a break.
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