Part of why Gossip Girl is so iconic is because there is so much to hate and to love simultaneously: Jenny’s smoky eye, the way Serena simply discards her cell phone in a public garbage can when confronted with a stressful text, how Nate never says a single interesting thing. The show’s iconic plot lines fall into that love/hate relationship, with some truly unhinged stories throughout its six-season run. Ahead, you’ll find some of our most absurd favorites.
Dan And Georgina’s Baby
Georgina showed up in the Humphrey loft pregnant and said she was having Dan’s baby. Dan stepped up to the role despite no paternity test, and big surprise — the baby ends up not being his. Georgina actually had an affair with a married Russian man, whose wife threatened to have her killed when she found out, but called off the hit after she said Dan was the father. Eventually, she just moved out of the loft and took the baby with her. And none of this was remotely interesting!
The Hillary Duff Threesome
In this iconic episode, Hillary Duff played a celebrity who went to NYU. On her last night, she, Dan, and Vanessa had a bucket list of things every college freshman must do, and the last item was a threesome. Duff finished her drink and then made out with Dan and Vanessa to a cover of T.I.’s “Whatever You Like.” Incredible.
Ivy Dickens AKA Charlotte Rhodes As A Concept
Possibly Gossip Girl’s most chaotic character, Ivy Dickens appeared in a whopping 30 episodes. Ivy was an actor hired by Lily’s sister to pretend to be her daughter, then she got the inheritance and then lost it and got it again? I think? At one point, she asked Dan to call her Serena, and it’s revealed she wasn’t taking her medication for bipolar disorder. But the most chaotic thing is that this girl dated Rufus and Serena’s dad.
After Blair spontaneously married a prince, he turned evil
Newly single Blair and Serena were enjoying adventures in Paris when Blair met the Prince of Monaco, Louis. After a speedy engagement, the two were wed and Louis quickly turned on Blair — using the marriage as a way to control Blair, while threatening to ruin her family financially if she filed for divorce. And of course, Chuck Bass was her knight in a shining tuxedo and bought her freedom from Prince Louis.
Prince Louis paid Chuck’s therapist to try to make him do something unhinged and lose Blair forever
To get Chuck Bass to open up to anyone is such a superhuman feat, so for as bad as he was, it’s a bummer he couldn’t even trust his highly-paid therapist. It backfired because when Blair found out, she said Louis was turning into Chuck. Get this girl some new men!
Serena thinking she killed that guy when they did coke
Serena’s iconic line “I killed someone” had maybe the worst payoff of any of Gossip Girl sentence. This was supposed to be the big reveal to why she fled the Upper East Side. Not only did she hook up with Nate while he was with Blair, but she “killed someone!” What really happened was she passed a guy a line of coke and he promptly overdosed as she called 911. Still dark.
The fact that two characters were “banished” from New York City
Leave it to the sinister magic of Blair Waldorf to be able to banish two women from ever setting foot in Manhattan again. Blair banned Jenny from New York after she had sex with Chuck, forcing her to move upstate. She came back in one episode for an interview with Tim Gunn, and Blair agreed to give her a “day pass” in exchange for her not coming back for the rest of the year. Brutal! And later, Chuck, Blair, Nate and Serena all banished Juliet from Columbia and Manhattan for trying to ruin Serena’s life. Maybe she could flee to Brooklyn?
The idea that the Humphrey family was poor
OK, they weren’t old money rich, but Rufus Humphrey was in the equivalent of maybe Jane’s Addiction, and he owned a three-bedroom loft in Dumbo and an art gallery that was usually empty. This member of Rolling Stone’s Top Forgotten Bands Of The ’90s certainly isn’t slumming it.
Serena’s dad tricking Lily into thinking she has cancer
In this absolutely bonkers plot, Serena’s dad Munchausened Lily into thinking she had cancer, when really he was giving Lily the wrong medicine to keep her sick so he could take care of her. The worst part is that they still ended up together at the end of the series.
The deaths(s) of Bart Bass
Bart Bass faked his own death in Season 2, only to reappear in Season 5 and explain that he paid the hospital to announce he was dead so his competitors wouldn’t go after Chuck and Lily. Then in Season 6, he and Chuck had a final Star Wars-esque showdown on the roof of the hotel, where Bart slipped and was hanging off the edge of the roof and Chuck let him fall. Dark!
Nate’s tabloid newspaper had a company jet
The New York Spectator became a major media company (thanks in part to Elizabeth Hurley as the unscrupulous reporter Diana Payne) but still — we’re supposed to believe a newspaper had a private jet in the year 2011, in the post-Recession media era? I don’t think so.
Serena fell in love with her teacher after putting him in jail
Lily forged an affidavit in Serena’s defense accusing Serena’s teacher, Ben, of assault, in order to ensure Serena’s transfer from the Connecticut boarding school back to school in New York. Through this, Lily was able to blackmail the boarding school into largely improving Serena’s grades. Leave it to Lily to break multiple laws to get her daughter home. This allegation left a pretty hefty dent on Ben’s criminal record, and while legally working to clear his name, he and Serena developed romantic feelings for one another. Serena always had an unconventional approach to finding her romantic partners.