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

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. 

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.

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.

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.

No one can deny Chuck's growth over the course of the series. He hits a particularly high point when he tells Blair to be with Prince Louis because he brings out the best in her, whereas Chuck only brings out the worst. He even starts to see a therapist to deal with his heartache after losing Blair.

However, the positivity is short-lived. It's revealed that Louis is actually paying Chuck's therapist. Louis wants her to turn Chuck back into an angry monster so Blair will never love him again. At this point, the Gossip Girl writers apparently discovered that physical aggression just wasn't doing the trick anymore, so they upgraded to psychological torment.

Thankfully, Louis is found out rather quickly and Chuck doesn't undo all his good progress. Still, interfering with someone's mental healing? That's quite a drastic move. And a therapist succumbing to a bribe? So much for helping people.

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.