Serena Van Der Woodsen hugging her boyfriend Dan Humphrey


All Of Serena Van Der Woodsen's Boyfriends, Ranked

Spoiler alert: Her best boyfriend wasn’t Dan.

Dudes love Serena Van Der Woodsen. The Gossip Girl anti-heroine dates a smattering of men across the show’s six seasons, most of whom are incredibly bad for her because she never really addresses her bigger emotional baggage, and also because she’s a teenager for most of the show. We’ve all been there, S! From her first love Dan to a Columbia professor, here are Serena’s boyfriends, ranked.

9. Ben Donovan

In this relationship that never should have made it past the writer’s room, Serena dates her former boarding school teacher. This is after Serena’s mom falsely accuses Ben of statutory rape, which gets him wrongly imprisoned, and Ben and his sister Juliet try to get revenge by ruining Serena’s life. Serena finds out what her mom did, gets Ben freed from prison and they decide it’s a great time to start dating.