Book Series
Serena van der Woodsen (girlfriend)
Vanessa Abrams (girlfriend)
Mystery Craze (fling)
Elise Wells (fling)
Monique (fling)
Bree (fling)
Greg (dated)

TV Series
Serena van der Woodsen
First Relationship:
Start Up: Pilot (101)
Broke Up: Woman On the Verge (117)
Reason: Serena lied to Dan and told him that she cheated on him.
segundo Relationship:
Start Up: Summer Kind of Wonderful (201)
Broke Up: The Dark Night (203)
Reason: The two realized they were in two different places.

Georgina Sparks
Start Up: Woman on the Verge (117)
Broke Up: Much "I Do" About Nothing (118)
Reason: Dan learned the truth about Georgina.