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The Most Ridiculous Storylines 'Gossip Girl' Writers Ever Came Up With

List RulesVote up the 'Gossip Girl' storylines that went off the deep end.

Gossip Girl, one of the most habit-forming shows of the 2000s (and it lives on via Netflix), features storylines that revolve around an elite group of rich kids (and a few less wealthy ones from Brooklyn) who attend a private school on the Upper East Side in New York City. The titular "Gossip Girl" is an anonymous online scribe who chronicles their every move, tabloid-style. The show isn't exactly relatable, yet viewers obsess over the craziest Gossip Girl moments, as well as the lives of these wealthy high schoolers who eventually turn into college students.

From the beginning, the show's details are questionable. High school students attending clubs and drinking at bars could hardly be considered realistic. As the years go on, however, the worst Gossip Girl storylines get more and more ridiculous. Eventually, the insanity of the show is almost too much to follow, much less explain to anyone who hasn't seen every episode.

While plenty of episodes remind viewers why they love the show so much, Gossip Girl's most shocking moments have a lot of fans questioning why they are still watching. Outlandish plots are common on many television series, but the worst Gossip Girl storylines deserve an extra-large eye roll. XOXO, everyone. And after you've voted, make sure to check out these great shows like Gossip Girl!

  • 1

    When Serena Dates Her Former Teacher After Putting Him In Jail

    Photo: Gossip Girl / The CW

    Serena's messed-up relationship with Ben Donovan goes all the way back to her boarding school days in Cornwall, CT, before the series even begins. She falls for Ben, who is one of her teachers. The two spend a lot of time together and develop feelings for each other. Although this is inappropriate because Serena is a high school student, Ben doesn't allow the relationship to become physical. Even though he turns Serena down, gossip about their relationship runs rampant at her boarding school. 

    Lily finds out about Ben and uses that information to transfer Serena back to a New York school, which is where we catch up with her in the series premiere. In the process, Lily opens an investigation into Ben, which leads to him being fired, accused of inappropriate relations with a minor, and put behind bars. All this happens without Serena's knowledge, because Lily forges her signature on an affidavit.

    Serena learns out about the whole situation years later and finds Ben to apologize. Despite all that history, the two start dating. Yes, they have an actual relationship, short-lived as it may be. Let's not forget Ben used to be Serena's teacher and his relationship with her put him behind bars. Then again, maybe you should forget it. Ben and Serena seem to get over it pretty fast. 


    Is this ridiculous?
  • 2

    When Elizabeth Fisher Both Is And Isn't Chuck's Mother

    Photo: Gossip Girl / The CW

    In Season 3, Chuck Bass uses his shares in Bass Industries to purchase the Empire Hotel. The new business venture quickly becomes Chuck's sole focus, until he meets a mystery woman at his father's grave. The woman, Elizabeth Fisher, eventually tells Chuck she's his mother. Meanwhile, Chuck's uncle, Jack Bass, arrives back in town. Jack tells Chuck that Elizabeth can't possibly be his mother because Jack was at Chuck's mother's memorial service. Chuck has a DNA test done and the results come back positive. Believing Elizabeth really is his mother, he signs over the hotel to her to avoid backlash from lawsuits.

    Elizabeth then reveals she was working with Jack all along to take the hotel from Chuck. She says she's not his mother, is in love with Jack, and plans to leave New York for good because she can't live with what she's done. However, in a final conversation with Jack, Elizabeth suggests she actually is Chuck's mother.

    So what is the truth? Is Chuck's mother alive or not? Is Elizabeth his long-lost mom or did they find a way to fake the DNA results? Unfortunately, we never really find out, making this whole storyline a confusing thread of the complex web that makes up Chuck's familial relationships.

    Is this ridiculous?
  • 3

    When William van der Woodsen Convinces Lily She Has Cancer

    Photo: Gossip Girl / The CW

    In Season 3, Lily supposedly spends the summer with her mother, CeCe, who’s being treated for cancer. Eventually, it's revealed that Lily was sick all along instead of her mother. Not only does she have cancer, but she's also being treated by her ex-husband, William van der Woodsen. Understandably, her current husband, Rufus, is angry about this arrangement. He insists William wants to win Lily back, and Lily agrees with him. 

    The web of lies is more complex, however. When Lily and Rufus confront William, they find out Lily never had cancer. In fact, it turns out William has been giving her pills to make her sick, forcing her to be dependent on him. He believes that if they spend enough time together, Lily will realize she was meant to be with him all along. He will magically cure her nonexistent cancer and they'll ride off into the sunset together.

    William wants to be with her so badly that he casually makes her sick for months and convinces her she has a life-threatening illness. That's not messed up at all.

    Is this ridiculous?
  • 4

    When Bart Bass Fakes His Demise To Avoid Being Slain By A Real Estate Competitor

    Photo: Gossip Girl / The CW

    Bart Bass is difficult to like, so when he perishes in Season 2, some viewers likely feel a sense of relief. His menacing personality is gone for good, eliminating his control over Chuck and opening the door for Rufus and Lily to be together. Imagine our surprise when Bart reemerges in Season 5 and explains he faked his demise.

    When Chuck finds out Bart is alive, Bart explains he had information about the unlawful activities of one of his competitors. The car mishap that supposedly ended him was arranged by this real estate mogul, who was trying to get rid of Bart before he could take the information to the proper authorities. When Bart realizes his life is in danger, he decides to use the car mishap as a cover to fake his own demise. He claims he was keeping both Chuck and Lily safe by simply disappearing.

    But what kind of real estate shenanigans could lead to such a drastic end? And why does Bart simply disappear for years, instead of finding a way to take down his competitor? More importantly, why doesn't he just go to the police? This storyline is all kinds of messy, and unfortunately brings Bart back into the picture - a turn no one is excited about.

    Is this ridiculous?