Central characters
Serena वैन, वान der Woodsen
Serena is described as 5' 7" with pale, long, blond hair and big, dark-blue eyes. She is slim and ethereally beautiful, often described as "perfect" in the books. She is very smart, but is often told that she is not working to her full potential. Her personality is not always as well regarded as her physical attributes. Like her sometimes best-friend Blair Waldorf, she and her family are prominent in New York society. Serena dabbled in modeling before landing a starring role in Breakfast at Fred's, a remake of Breakfast at Tiffany's. Serena has kept...

Flings and romantic relationships

Book Series
Blair Waldorf (on and off girlfriend/lover)
Serena वैन, वान der Woodsen (ex-lover)
Jenny Humphrey (ex-girlfriend)
Georgina Sparks (ex-girlfriend)
Lexie (fling)
Tawny (fling)
L'Wren (fling)

TV Series
Blair Waldorf
First Relationship:
Start Up: Before Pilot (101) (They are कहा to have been dating since kindergarten.)
Broke Up: Victor, Victrola (107)
Reason: Blair confronts Nate about his confession to 'Serena'.
Second Relationship:
Start Up: Hi, Society (110)
Broke Up: School Lies (112)
Reason: Chuck threatens to tell Nate about their relationship if Blair...

Flings and romantic relationships

Book Series
Nate Archibald (lovers/dated)
Miles (fling)
Owen Wells (fling)
Lord Marcus Beaton-Rhodes (dated)
Jason (fling)
Erik वैन, वान 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 मास्करेड ball.
Second Relationship:
Start Up: Hi Society (110)
Broke Up: School Lies (112)
Reason:...