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Dan Humphrey Relationships


Serena van der Woodsen

First Relationship:
Beginning: "Pilot" (101)
End: "Much 'I Do' About Nothing" (118)
Reason: Serena lied for too long about her 'secret.'

Second Relationship:
Beginning: "Summer Kind of Wonderful" (201)
End: "The Dark Night" (202)
Reason: There were too many things that happened that they couldn't move on from.

Third Relationship:
Beginning: In the Realm of the Basses" (214)
End: "Carnal Knowledge" (217)
Reason: Serena was too quick to believe that Dan cheated on her with Rachel.

Georgina Sparks

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

Rachel Carr

Start Up: Carnal Knowledge (217)
Broke Up: The Age of Dissonance (218)
Reason: Dan found out Rachel sent negative information to Yale about Blair and Blair wasn't able to attend Yale.
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