Serena's love life on Gossip Girl was complex, with boyfriends ranging from con artists to best friends to former teachers. Her significant others didn't just come from her social circle but also from her travels, adding to the drama of her romantic life. Serena's relationships were filled with lies, scandals, and manipulations, but some boyfriends showed genuine care and support.

Serena van der Woodsen was a true icon on Gossip Girl, with a dating history of boyfriends that was just as complicated as it was exciting. Since the dissolution of her relationship with Dan in season 1, she has dated a plethora of men, some of whom included her childhood friends, former teachers, con artists, politicians, and then Dan (again).

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When she wasn't looking for Gossip Girl's identity or charting her own unique path in a world of privilege and traditions, her love life was a...