Happy 18th birthday, Gossip Girl! She’s finally a legal adult — something none of the main characters were when they were getting wasted in bars and strip clubs, hooking up with 40-year-olds, buying hotels, ruining lives, etc. Gossip Girl remains one of my favorite shows of all time because it’s so realistic and relatable. It’s like watching a documentary about my own life.
I kid, I kid. There’s truly never been a more insane show on the air, and all six seasons belong in the pop culture history books. Even after 47 or so rewatches, I haven’t had enough of these disgustingly wealthy icons and their fabulous, chaotic, concerning city lives. (Plus, Blair Waldorf is my North Star, so it’s crucial that I continue to study her.)
From Georgina’s Jesus era to Blair marrying an evil prince, here’s my ranking of the most unhinged Gossip Girl plot lines.
Gossip Girl Most Insane Moments Ranked
6. Dan Being Gossip Girl
There are a million and one reasons why it makes zero sense that Dan is Gossip Girl, but I’m obsessed with the writers just randomly deciding that in the final episode. Dan spreads nasty rumors about himself and his little sister, which is psychotic. Plus, he’s shown looking genuinely shocked at several GG blasts throughout the series. The math just isn’t mathing.
In the series finale, the “poor” Brooklyn native claims he became Gossip Girl in order to write himself into the elite Upper East Side world… Serena’s world. Supposedly, it was all about gaining power and pulling the strings from behind the scenes. (TBH, I think the writers just needed a Gossip Girl and they needed her to be one of the main characters.)
“It wouldn’t have made sense for anybody,” Penn Badgley pointed out during his Call Her Daddy interview. “We all wanted it to be Dorota.” Now, that would’ve been incredible.
5. Georgina’s Jesus Camp Era
@urlocalwaldorf I haven’t been to Church in 6 years #georginasparks #Jesuslovesyou #fyp #viral #relateable #florezelia ♬ original sound – r🕊️
The writer who dreamed up Georgina Sparks’ Jesus era deserves some kind of award. ~Bitch to Bible and back to Bitch~ is one of the greatest character arcs I’ve seen on television. When the core crew needs help exposing Gabriel and Poppy (who are scamming Serena’s family), they track down Georgina for backup. It’s a solid plan, considering she’s pretty much evil/chaos/manipulation embodied.
But they’re shocked to discover their old nemesis at bible camp, saying shit like “I gave up my old ways when I let Jesus take the wheel” and “I will not perjure myself in front of the lord.” It takes lots of convincing, but eventually, Georgina agrees to go back to NYC and help out with the Gabriel and Poppy situation. The taste of drama brings her right back to her wicked roots, and we get the most iconic line of the series: “You can tell Jesus that the bitch is back.”
RIP, Michelle Trachtenberg ❤️.
4. Nate And The Duchess
@ggxoxo70 #gossipgirlhere #gossipgirl #gg #blairwaldorf ♬ original sound – GGxoxo
Nate’s love life is… never boring and always distressing! In season 2, he has an affair with Catherine Beaton, the Duchess of Beaton. She’s an adult married woman, and at this point, he’s 17. Super not okay. When Nate’s family runs into money problems, Catherine pays him to keep hooking up with her. And somehow, it gets worse even from there! Turns out, Catherine’s also sleeping with her stepson. Of course, Blair eventually saves the day by blackmailing Catherine into paying off Nate’s family’s debt.
This whole storyline is only slightly more insane than Nate hooking up with Diana (another woman decades older than him) who also happens to be his boss at The Spectator. Oh, and then becoming editor-in-chief of said publication… at like, 21?
3. Blair Marrying A Psycho Prince
Only Blair Waldorf goes on a Paris vacation and returns with a literal prince. The NYC princess and Prince Louis Grimaldi of Monaco fall for each other in the city of love and before long, they’re back in Manhattan and engaged.
But Blair’s soulmate, Chuck just can’t stay away, of course! He keeps interfering with the engagement, and eventually, the two admit they’re still in love. Sadly, Blair and Chuck get into a terrible car accident, which leads to Blair finding God and making a desperate pact: if Chuck survives, she’ll marry Louis.
She goes through with the batshit plan, but Gossip Girl crashes the wedding ceremony by sending everyone a video of Blair telling Chuck she loves him. Although Blair and Louis do get married, Louis makes it clear that he fucking hates her. During their first dance, he whispers: “There is nothing between us but a contract. Our marriage is all for show, and you’re going to put on the best damn show anyone ever has.” Nightmares. Blair and Louis eventually divorce (thank heavens).
2. Serena And Dan Sharing A Brother
Ya know, I shouldn’t even complain about the Belly-Conrad-Jeremiah love triangle feeling incesty, because Serena and Dan’s situation is at least 100 times worse. Not only are their parents in love (Rufus and Lily dated back in the day and eventually get married in Season 3), but they also share a son. So, Serena and Dan share a brother, Scott.
Lily secretly gave him up for adoption without even telling Rufus. Years later, Scott finds Dan and pretends to be a student at NYU to get to know him. (Because in Gossip Girl, god forbid anyone just tell the truth.) Of course, it’s Georgina who blows the whole thing up — at Rufus and Lily’s wedding.
Mind you, Dan and Serena still end up together at the end of the series, because they’re not okay. Deeply unwell people.
1. Dan And Georgina Raising A Baby
As if Dan and Georgina hooking up wasn’t unhinged enough, they also have a (brief and jarring) mommy and daddy moment. In the season 3 finale, Georgina drops some absolutely gobsmacking news on Dan: She’s nine months pregnant and the baby is his. Or so she says.
Naturally, Georgina ditches her son and her alleged baby daddy, and Dan continues to bond with baby Milo… until he finds out that that kid is not his biological son. My guy, you really believed Georgina? Concerning.
