17 Super Messed-Up Things That Happened On Gossip Girl

Gossip Girl is hands-down one of the wildest shows of all time. There were horrible relationships, friends betraying each other, violence against women, and a whole bunch of scandal. All of the characters are awful in their own special way, and it’s especially hard to watch now, knowing that Ed Westwick is allegedly a real-life piece of trash.
While we loved some of the drama, there were certain moments that were unbelievably messed-up, even for Gossip Girl. So, here are 17 of the most absurdly twisted moments in this CW show’s history.

17. When Chuck assaulted Serena

Gossip Girl pretty much started by showing us exactly what was in store for the rest of the series: Chuck assaulting women. In the first episode, his character starts off strong by trying to rape Serena. Great. It all starts when he tries to “help” Serena because she’s blackout drunk. He takes her to the kitchen of his dad’s hotel, gets her a grilled cheese, and sits her on the counter. Aaaand then he forces himself on her. He forcibly kisses her and starts grabbing at her, and doesn’t stop until she kicks him in the groin.

16…and then he does the same to Jenny

Honestly, almost every problematic thing that happens on Gossip Girl involves Chuck Bass in one way or the other. Later in the episode, after the whole Serena thing, there’s a party. Jenny shows up (a 14-year-old!) and is obviously wooed by Chuck. He’s rich, handsome, and talks in a low/whispery voice. Things almost immediately begin going horribly. He takes her to the roof and forces himself on her. He is only stopped when Dan and Serena run to the roof to stop him. Ugh.

15. When Chuck hooks up with Blair but she thinks it’s the Duke

Yet again, Chuck proves why he’s one of the scummiest TV characters of all time. In season two, his obsession with Blair gets completely possessive and out of control. He does pretty much everything in his power to ruin things for her, and manipulate/blackmail her into dating him. Super charming. Anyways, he knows her relationship with the Duke isn’t going well ~sexually~, so he tries to seduce her. She rejects him, so he comes to find her in her pitch black room, speaking in a British accent. They begin hooking up because Blair thinks it was the Duke. Ummmmm?

14. When Georgina outs Eric

Okay, the way Gossip Girl has handled LGBTQ+ issues is… Less than ideal. No episode shows this better than when Georgina, who is arguably the evilest TV character of all time, outs Eric to his family at the dinner table. It’s all part of her sick plot to ruin Serena’s life, and her entire family’s as well. First of all, Eric’s like 14 when this happens, and has had issues with depression and suicide attempts. Her outing him to his less-than-accepting mom (another huge UGH) was way too far, even for Georgina.

13. When Dan hooked up with Georgina

Can we all just agree that Dan sucks? Like, even when Gossip Girl first started, when he was supposed to be a “””good guy””” and sympathetic character. He’s always been incredibly judgy, annoying, and whiny. Case in point — he’s moping around like an idiot because Serena won’t tell him what’s going on in her life, even though she’s clearly dealing with a lot. He just wants everything to be about HIM. So they end up breaking up, and literally within hours of the breakup, he hooks up with Georgina. Granted, he doesn’t know her full story at that point, but either way, it’s super slimy.

12. When Chuck took Blair’s virginity

GOSH, when will Chuck stop being the hands-down worst character on Gossip Girl? Answer: never. He loves taking advantage of vulnerable girls, especially when there’s alcohol, revenge, and lies involved. After Blair and Nate break up (BTW, Nate is also Chuck’s best friend), Chuck immediately pounces. He knows Blair is upset, and she’s also pretty drunk. They immediately begin hooking up, and she has sex for the first time with Satan himself. He also totally knew Blair would regret it, and Nate would be devastated.

11. When Chuck made Blair sleep with his uncle

In another one of Chuck’s most disgusting moments, he manipulated his own girlfriend into sleeping with someone else. Not just anyone, though, his own Uncle Jack. In order to get Jack to sign off on Chuck’s business deal, Jack wanted to spend a night with Blair. To make it seem like Chuck wasn’t involved, Jack pretended to run into her at a store, and then essentially said that he would give Chuck what he wanted in exchange for a night with Blair. Blair agreed because Chuck had her under his complete control, but Chuck set the whole thing up! So scummy.

10. When the Duchess blackmailed Nate into staying with her

…And who could forget, the Duchess AKA Catherine Beaton? She was only on Gossip Girl for a little bit, but man, oh man, was she awful. Basically, we meet her as the older, married woman that Nate is having an affair with in the Hamptons. So not only is she totally cheating on her husband, she’s doing it with a high schooler. Then, when Nate wants to end things, she completely blackmails the younger man. The only reason they keep sleeping together is that she threatens to tell the government where Nate’s dad is hiding. So, total coercion.

9. When Chuck physically abuses Blair

To no one’s surprise, things between Chuck and Blair continued to go horribly. The worst moment? When Chuck completely loses his temper and ends up pushing Blair to the ground and punching the glass window behind her. She gets a cut on her face and is clearly unbelievably terrified. Chuck was freaking out because Blair announced her engagement to another man. Of course, the only natural response for Chuck is screaming “you’re MINE” in her face. The whole thing was incredibly disturbing.

8. When Blair’s mom gets mad at her for having an eating disorder

To no one’s surprise, Gossip Girl didn’t do a great job handling sensitive issues such as eating disorders. In the first season, we learn that Blair struggles on and off with bulimia. Instead of being concerned and understanding, her mom basically yells at her for it. Eleanor is mostly just worried that someone will find out and it will ruin her image. Thus she tells Blair to keep it under wraps and seek treatment immediately for the sake of Eleanor’s popularity. Mother of the year!

7. When Asher Hornsby calls Eric a gay slur

Granted, it was great that Gossip Girl tried to have a little bit of representation, but pretty much everything related to Eric being gay turned out badly. For example, we find out that he’s hooking up with Jenny’s then-boyfriend, Asher Hornsby. When Eric calls Asher out for cheating and confronts him about their relationship, Asher replies in the worst way possible. He shouts that Eric is the F-slur in front of a whole party. It’s… unbelievably upsetting.

6. When Blair said Serena had a drug problem

Okay, so basically this all happened at the beginning of Gossip Girl when Serena and Blair were first reunited. Their friendship was falling apart, and they spent all of their time trying to tear each other down. To finally beat out Serena, Blair decided to tell a room full of college scouts that Serena had a drug problem, which she said she could prove with pictures of Serena outside of rehab. First of all, joking about addiction? Yikes. Second of all, it turns out that the reason Blair spotted Serena outside of the rehabilitation center was that Serena’s brother was recovering there after attempting suicide. It was truly hard to watch.

5. When everyone thinks Serena has an STI

This was especially messed up after we all learned that Dan was, in fact, Gossip Girl. Which means that he was the one who told the entire Upper East Side that Serena had an STI. Mind you, this all happened at a time when Dan was trying to win Serena back. The whole thing is just weird and creepy, and another one of Gossip Girl’s invasions of someone’s personal life that was just a little bit too far. Plus, it makes no sense that Dan is GG because later his relationship with Vanessa is ruined after a photo of him at a Student Health Clinic. But that’s an issue for another day.

4. When Dan writes about his sister’s sex life

Okay, so this is another one of the Dan-being-Gossip-Girl-makes-very-little-sense-and-is-super-f*cked-up things. Back during season one, Gossip Girl posts about Jenny allegedly losing her virginity to Asher… which is a little weird considering you’d think a big brother would have SOME sort of loyalty to his flesh and blood. But IF he’s the real GG, then he’s the one who authored these words about his little sis: “Breaking News – Asher Hornsby overheard bragging that Little J swiped her V card at his register. Didn’t anyone teach you, Little J? You shouldn’t give away the ending if you want him to pick up the book again.” …More than a little awkward.

3. When Dan had an affair with his teacher

This is all-too-common on teen TV shows: the teacher affair. We saw it with Ezra and Aria on Pretty Little Liars, Archie and Miss Grundy on Riverdale, and Pacey and Tamera on Dawson’s Creek. So it makes sense that a show as messed up as Gossip Girl would also have a really shady teacher-student story line. Basically, Rachel is a teacher at Constance Billard School for Girls, which is the sister-school for Dan’s high school. It just so happens Dan and Miss Carr are sleeping together — a piece of information that Blair leaks to Gossip Girl when she’s feuding with the teacher. Eventually, Miss Carr flees home to Iowa. But still.

2. When Georgina tried to film Serena having sex

In another one of Georgina’s worst moments on Gossip Girl, she filmed Serena hooking up with someone without her permission. While we never truly know if Serena and this guy ended up having sex, we do know things got pretty intimate. The beginning of the tape starts with Georgina hooking up with the guy and joking about how Serena will “never know” that she’s being filmed. Plus, she spends the whole time teasing Serena and basically shaming her for being slutty. The whole thing is very disturbing and an A+ example of rape culture.

1. When Dan totally slut-shames Serena

Time and time again, Dan proved to be one of the worst boyfriends ever. Granted, there are few good men on Gossip Girl, and it would’ve been really hard to be worse than Chuck. But he had the most absurdly-high expectations for Serena, demanded all of her time, was completely judgemental and refused to even try and understand her life. Before they had even had their first date, he gets furious at Serena after he finds out she’s slept with Nate. He says, “I thought you were different than that.” Um, relax.

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