Serena van der Woodsen Relationships

Nate Archibald

One Night Stand
Reason: Serena put her feelings for Nate aside because she felt guilty about hurting Blair and didn't want to lose her best friend.

Aaron Rose

Boyfriend
Beginning: "Pret-A-Poor J" (208)
Broke Up: In between "O Brother, Where Bart Thou?"(213) and "In the Realm of the Basses" (214)
Reason: Serena wanted to be with Dan.

Gabriel Edwards

Boyfriend
Beginning: "Seder Anything" (221)
Broke Up: "Southern Gentlemen Prefer Blondes" (222)
Reason: Gabriel had vanished with all the money that certain people invested in his project.

Dan Humphrey

Boyfriend
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" (203)
Reason: There was 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 had cheated on her with Rachel.