A decade after its season finale, Gossip Girl is still one of the most iconic teenage series ever created. Its broad cultural impact not only helped launch Blake Lively’s and Penn Badgley’s careers, but it is also responsible for greatly contributing to the genre. Amazing series like Elite, Euphoria, and Pretty Little Liars, for example, wouldn’t exist without the CW series.

However, even if Gossip Girl managed to craft an entirely new aesthetic for teen drama television, the series is not without its flaws. In fact, several things in Gossip Girl don’t make sense, especially its random couplings. Romances in Gossip Girl often include wide age gaps, ridiculous pairings, and unlikely connections with other characters. Of course, it is all part of keeping the audience interested, but sometimes they take it too far, and some Gossip Girl couples are truly bizarre.

10

Blair and Dan Was a Weird Combination

Dan and Blair’s Relationship Begins in Season 5, Episode 17, “The Princess Dowry”

Blair and Dan stand together in Gossip Girl.

From the very beginning of Gossip Girl, Blair and Dan were the most different characters in the group. Blair was also disgusted by Dan because of his lack of style or ambition. At the same time, Dan always found Blair too shallow. Funny enough, they were Serena’s closest people, so they had to hang out a lot.

In a weird storyline, Blair and Dan get closer while worrying about Serena. This leads to actually developing romantic feelings for each other, which totally puts off the audience. Dan is Serena’s endgame, and Blair is her best friend, so it didn’t make any sense in chemistry, ethics, and especially plot-wise, for them to be together. Gossip Girl had a hard time drawing a line in which couplings make sense, and the writers had no issue getting the characters to date everyone in the series. Blair and Dan were the last straw.

9

Catherine and Nate Are a Controversial Romance

Nate and Catherine’s Relationship Begins in Season 2, Episode 1, “Summer Kind of Wonderful”

Catherine Beaton holds Nate's face by the chin in Gossip Girl.

Catherine and Nate’s relationship is simply revolting, and it has no place in a series that’s supposed to be relatable to teenagers, up to a point. Catherine Beaton is a Duchess and a middle-aged woman who sleeps with Nate when he’s only 17 years old. She even pays him for intercourse when Nate is struggling financially.

Blair and Dan together, Bart Bass, and Dan Humphrey in Gossip Girl

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When Catherine realizes that Nate is crushing on Vanessa, she blackmails him to stay with her. She will tell the FBI about Nate’s father if he dumps her. To make matters worse, Vanessa later finds out that Catherine is sleeping with her stepson, Marcus, who is also dating Blair. The relationship is weird age-wise, and it also involves some nasty power dynamics, but it also gets very convoluted when the show decides to involve other characters amidst the chaos. Basically, it’s drama, for drama’s sake.

8

Chuck and Elle Lasted 1 Episode & Went Nowhere

Chuck and Elle’s Relationship Occurs in Season 2, Episode 18, “The Age of Dissonance”

Chuck Bass smiles outside the courtroom in Gossip Girl.

Elle only appears for one episode, but her storyline is unnecessary and it goes nowhere. Elle used to be Chuck’s nanny, and Chuck recognized her when she was having dinner with Carter. Elle explains to Chuck that she’s in a difficult position and needs his help. Chuck tries to help her, giving her a fake passport and helping her leave the United States. However, she’s abducted by Carter when Chuck misplaced his trust. In the end, Elle is never in danger, and when she gets a comfortable sum of money from Carter’s illegal club, she confesses to Chuck that she was using him.

A problem with Chuck and Elle’s relationship is that it comes out of nowhere and doesn’t add anything to the show. Chuck simply gets infatuated with this woman he hasn’t seen in years. The plot is never addressed again, and it seems more like a ploy to keep Blair and Chuck separated.

7

Steven Spence and Serena Are a Match Made in Hell

Steven and Serena Start Dating in Season 6, Episode 1, “Gone Maybe Gone”

Steven and Steven Pence hug each other in Gossip Girl.

At the beginning of Gossip Girl‘s sixth season, Serena is dating an older man. She’s living in his summer house, and he thinks her name is Sabrina. Even though he discovers she’s been lying to him, the two continue dating in NYC. Things get particularly weird when it turns out Steven is the father of a 17-year-old girl who is dating Nate. In one episode, Gossip Girl includes two of the worst age-gap relationships on television.

A middle-aged man with a 20-year-old woman wouldn’t be surprising — if not okay — in the real world. However, the fact that his daughter is seeing Serena’s former lover makes things particularly absurd. To make things worse, it turns out that, at some point, Steven and Lily also had a sexual relationship in the past. There are too many coincidences and bizarre connections, even if the Upper East Side is a tiny place.

6

Georgina and Dan Are Simply a Ridiculous Match

Dan and Georgina Have Sex in Season 3, Episode 1, “The Freshmen”

Georgina is likely the most terrifying villain mastermind in Gossip Girl. Funny enough, like most antagonists in the series, she eventually becomes part of the group—not without creating flabbergasting amounts of drama first, though. Georgina tries to ruin Serena’s life several times, especially in the first season. She blackmails Serena with a tape of her using drugs with an overdosed man. At the same time, she also befriends Dan, who was dating Serena at that point, and assumes a fake identity.

Savannah Smith, Blake Lively, and Michelle Trachtenberg in Gossip Girl

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This, however, didn’t stop Dan Humphrey from sleeping with Georgina. Not only is this out of character for a man who values honesty so much, but it’s also kind of improbable. Would anyone date the same person who lied about who they were to manipulate them and tried to hurt their ex-girlfriend? Not only that, but the plot becomes even more ridiculous when Georgina comes back with Dan’s alleged baby, who later on wasn’t Dan’s baby, but Dan raised the baby for a couple of months either way.

5

Serena and Ben Donovan’s Relationship Defies Many Social Conventions

Ben and Serena Start Dating in Season 4, Episode 14, “Panic Roommate”

Serena and Ben are at a high-end event at Gossip Girl.

In the fourth season of Gossip Girl, Serena is in the middle of a drama involving her new boyfriend, Colin Forrester, Nate’s conquer of the month, Juliet Sharp, and Serena’s old teacher, Ben Donovan. In the beginning, no one knew all these characters were related. Soon enough, it turns out Juliet is Ben’s sister, and she’s trying to get revenge on Serena. Colin is Juliet and Ben’s cousin, but he isn’t aware of her scheme.

As the season unfolds, Serena figures out that her old teacher is in jail after Lily forged her signature confirming that Ben had sexual intercourse with the teenage girl. As soon as Serena finds out, she works to get Ben out of jail. This is pretty decent, and the right thing to do; what is weird is that Ben and Serena end up dating. It is a bizarre outcome for Ben to date the girl whose family got him in jail for allegedly having sexual relationships with her when she was too young, especially when her ex-boyfriend was his cousin. Plus, the age gap.

4

Chuck Assumes Another Identity When He Meets Eva

Chuck and Eva Start a Relationship in Season 4, Episode 1, “Belles de Jour”

Chuck and Eva look at each other in Gossip Girl.

Chuck meets Eva, a French woman who saves him after he gets shot. However, things get weird when Chuck pretends to be a regular person. Chuck goes by the name of Henry Prince and works at a bar, a job that Eva found for him. The two even live together in a small apartment in France.

It might make sense that Chuck wanted to distance himself from Manhattan, but he could have done that without crafting a whole new identity. Eventually, Blair convinces Chuck to come back and he comes clean to Eva. Chuck brings Eva to the Upper East Side where Blair does everything in her power to make her life miserable. The only thing that makes sense about this couple is Eva getting tired of the situation and leaving Chuck.

3

Rufus and Ivy Is as Ridiculous as It Gets

Rufus and Ivy Start Dating in Season 6, Episode 1, “Gone Maybe Gone”

Rufus and Ivy sit in Rufus' kitchen in Gossip Girl.

Apparently, the Humphrey men have a soft spot for getting into relationships with con artists. Ivy, previously known as Charlie, was hired by Carol Rhodes to pretend to be her daughter and get CeCe’s trust fund. Eventually, her identity was revealed and Lily and Carol took her money away.

Split image of Blair dancing with Louis, Serena and Blair looking into a phone, and Blair and chuck embracing in Gossip Girl

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This wasn’t the end of Ivy’s storyline, though. In an attempt to get revenge on Lily, Ivy seduces Rufus, and it works. The fact that Rufus decided to date a woman that he once considered his niece, that he knew scammed Lily’s family, and that was half his age is both disgusting and ludicrous. And, of course, it wouldn’t be a Gossip Girl romance if there wasn’t some sort of twisted, incestuous connection, so it’s important to know that, at some point, Ivy also kissed Dan.

2

Sage and Nate Should Not Have Happened

Sage and Nate Start Dating in Season 6, Episode 1, “Gone Maybe Gone”

Nate and Sage walk together at a gala event in Gossip Girl.

If it wasn’t enough that Gossip Girl‘s sixth season only had 10 episodes to conclude the entire series, it also included a bunch of new and random characters. Sage Spence, daughter of Serena’s boyfriend Steven Spence, dates Nate. The girl is 17 years old and still in high school, while Nate is a full adult, around 21 or 22 years old, with a stable job. The age gap is disturbing, but the relationship is entirely unnecessary.

In a series that tries to wrap up each character’s development, it makes no sense to include a controversial romantic character who will not help conclude the series. Sage not only puts Nate in a bad light but also undermines his character development. In the end, Nate doesn’t end up with any of the characters, which is disappointing, seeing as he probably dated the entire cast.

1

Serena and Dan’s Endgame Is Completely Absurd

Dan and Serena Get Married in Gossip Girl’s Series Finale, “New York, I Love You”

Dan and Serena’s relationship is arguably the emotional axis of Gossip Girl. The show begins when the characters meet as Dan and Jenny try to fit in on the Upper East Side. The Shakespearean romance becomes the main drive of the series as Serena finds grounding in the boy outside her own inner circle. Serena’s deep admiration for Dan is rooted mainly in his lack of interest in high society. Dan tends to question the banality of Serena’s world, which she finds refreshing, even if challenging at times.

However, in the sixth season of Gossip Girl, Dan reveals that he was the voice behind the gossipy website all along. This meant that Dan was a little bit more concerned about the shallow world that he insisted on hating. Not only that, but it also shows that Dan was a little big-time stalker. It’s senseless that Serena still chose to marry a man who lied to her, publicly humiliated her for years, and was very different from what she initially thought.



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