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

Jessica Bedewi
225 votes 44 voters 14 items

List Rules Vote 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.

1
When Serena Dates Her Former Teacher After Putting Him In Jail
When Serena Dates Her Fo... is listed (or ranked) 1 on the list The Most Ridiculous Storylines 'Gossip Girl' Writers Ever Came Up With
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. 

 

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2
When Elizabeth Fisher Both Is And Isn't Chuck's Mother
When Elizabeth Fisher Bo... is listed (or ranked) 2 on the list The Most Ridiculous Storylines 'Gossip Girl' Writers Ever Came Up With
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.

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3
When Serena And Dan Date While They Are Step-Siblings
When Serena And Dan Date... is listed (or ranked) 3 on the list The Most Ridiculous Storylines 'Gossip Girl' Writers Ever Came Up With
Photo: Gossip Girl/The CW

The complicated dynamic between Serena van der Woodsen, Dan Humphrey, Lily van der Woodsen, and Rufus Humphrey is enough to make anyone's head spin. Lily and Rufus date when they are young, but break up because Lily's family disapproves. They reunite when their children, Dan and Serena, start dating. Although the chemistry between Lily and Rufus is clear, they don't act on their feelings because they want to respect their children's relationship. That doesn’t last for long though. 

In Season 3, Lily and Rufus get married. At that point, Dan and Serena aren't together. However, over the next few complicated years, Dan and Serena definitely have some romantic moments while their parents are married. They feel it’s obvious they’re meant to end up together, all the while refusing to recognize they’re technically part of the same family. 

Dan and Serena also share a sibling. Lily and Rufus had a child during their first relationship whom they gave up for adoption. Serena and Dan don't technically share blood, but they’re really hovering over the line of what’s appropriate and what’s not. As a general rule, it's not wise to date your step-sibling.

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4
When Dan Gets A Story Published in 'The New Yorker' As A High School Junior
When Dan Gets A Story Pu... is listed (or ranked) 4 on the list The Most Ridiculous Storylines 'Gossip Girl' Writers Ever Came Up With
Photo: Gossip Girl/The CW

According to Gossip Girl, success comes easy in New York City, especially if you're rich. But the success these teens experience is totally unrealistic. No storyline drives that point home more than Dan Humphrey getting a story published in The New Yorker as a high school junior. 

Dan Humphrey aspires to be a writer, and we're made to believe he has some talent. However, getting a story published in The New Yorker? That we can't believe. The New Yorker is a distinguished magazine with a history of exclusivity. Even well-known writers struggle to have their stories published in its pages. The idea that the magazine would accept a submission from a high school junior is preposterous.

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