Culture
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.
8. Tripp Vanderbilt
Serena has a brief affair with Nate’s married Congressman cousin because...of course she does. After Tripp’s wife catches them, she encourages them to keep seeing each other in secret to avoid the scandal of a divorce, which Serena isn’t happy with. Also, in a very upstate-Chappaquiddick moment, Tripp ditches Serena unconscious after a car wreck to make it look like she was driving. God, this dude sucks.
7. Max Harding
The Charlie-Ivy saga gets even messier when Serena briefly dates Charlie’s hot chef ex-boyfriend Max, who seems like a nice enough dude who was just looking for some funding for his restaurant and ended up getting swept in some Upper East Side antics — but then he blackmails Ivy by threatening to tell everyone she’s been lying about who she is. Thank you, next!
6. Gabriel Edwards
We as a culture don’t talk enough about how Serena dated Armie Hammer in Season 2 (she dodged a bullet there!) and we also don’t talk enough about how Serena dated a real live grifter. Man, finding love on the Upper East Side is hard enough without worrying someone is dating you to steal your money.
4. Aaron Rose
Aww Serena found a little indie boy! Besides being a noted short king, Aaron is also an artist who uses Serena as his muse, a career for which she was born. Also he creates a photo installation that projects live footage of them making out into Times Square, prompting the Kristen Bell voiceover to proclaim that “they’re bringing the sexy back to Times Square.” Not quite — but we love the effort!
2. Dan Humphrey
Serena and Dan end up together, which doesn’t make any sense. Dan is possessive; Serena is flighty, and their anxious-avoidant attachment styles clash at every turn. They also share a sibling. But we’ll allow it because we’re still coasting on the good energy of early summer’s Cancer season and because Dan has at least enough self-awareness to know he’ll never date anyone as hot as S.
1. Nate Archibald
Sure, getting into a relationship by cheating with your best friend’s longterm boyfriend isn’t the strongest ground for a relationship to stand on. But Nate and Serena are both old money, secretly love a scandal and ultimately want to spend their live jetsetting and cheating on each other with wildly beautiful people — a match made in Upper East Side heaven!