Top 20 Gossip Girl Plot Holes You Never Noticed

#20: Masquerade Face Blindness

It’s an ancient trope, to be sure. But that’s why we’re wondering why a show from 2007 would even employ it. In this episode, Blair throws a masked ball, and love drama ensues. Dan sneaks into the party, and Jenny steals Chuck’s clothes, leaving him in his underwear on the roof. But when Jenny switches masks with Serena. This causes Nate to confuse her for Serena. He stops her to dramatically confess his feelings. Jenny flees, but not before Nate kisses her. A simple confusion of masks doesn’t explain how Nate could have mistaken Jenny with Serena, as they are two different blondes with different voices and personalities. But hey, that’s “Gossip Girl” for you.

#19: Phone Inconsistencies

Cell phones and texting in general play a big role in the show, with characters getting messages and “Gossip Girl” blog notifications all the time. So it’s no surprise that there are some inconsistencies when it comes to the Upper East Siders' cell phone use. In a dramatic moment from Season 1, Serena throws away her cell phone… only for her to still have one in later episodes. It’s hard to conceive of Serena van der Woodsen rifling through the trash can, but it seems that is indeed the case. There is also one episode in Season 5 where Serena talks to Dan on her iPhone… while it’s clearly on the home screen. Oops.

#18: Blair Neglecting Her Royal Duties

This show is known for its wild storylines. But perhaps one of the wildest is Blair dating and even getting engaged to a prince, Louis Grimaldi of Monaco. Royalty still exists, of course, although an Upper East Sider actually marrying a prince is some extraordinary luck indeed. That said, real-life royalty does require a lot of rules and responsibilities that Blair doesn’t seem to be at all hampered by. In fact, once Louis tells her their marriage will be a loveless one by contract, Blair manages to evade it by running away with Dan. So much for a fairytale wedding.

#17: Harvard or Columbia?

College is a big deal on the show, until it’s not (but that’s another story). Still, in the early seasons, Serena and Blair apply to various Ivy Leagues, waiting with bated breath for their results. Where Serena’s dad went to college, however, is uncertain. In Season 1, Serena reveals her dad had been a Harvard man. However, while in Paris in Season 4, Serena reveals her legacy at a different Ivy. Which is the real story? It’s a minor discrepancy, all things considered. And to give the show the benefit of the doubt, it’s possible to go to two universities, one after the other.

#16: Who Is Chuck’s Mom?

The storyline with the mystery of Chuck’s mother is riddled with inconsistencies. In Season 1, Chuck speaks about his mother as if she were alive, but then it is mentioned she is, in fact, dead. In Season 2, Chuck clarifies that his mother died giving birth to him. Except no. In Season 3, he spies a mysterious woman named Elizabeth Fisher. She tells him she was nineteen when she got pregnant with Chuck, and she wasn’t ready to be a mother. Then it is revealed that Elizabeth was, in fact, an impostor and that she wasn’t his mother. Then Diana Payne falsely confesses to being Chuck’s mother, but it’s really actually… Elizabeth? We’re scratching our heads too.

#15: How Did Chuck Lose His Virginity?

He is, indeed, Chuck Bass. But even for a notorious womanizer, you’d think he’d get the story of how he lost his virginity straight. In Season 1, Blair mentions that Chuck lost his virginity to Georgina Chapman, with Chuck clarifying it was in the sixth grade. But then in Season 2, during the reading of his father’s will, Chuck snarkily reveals a different version of events. Which is it, Bass? We’d love to think it was with Georgina Chapman in the sixth grade over the alternative. But considering how Chuck Bass came out, perhaps the Italian au pair is the most realistic story.

#14: Vanessa Somehow Knew About Serena’s Affair

In an episode of Season 4, Serena comes clean to her therapist about her boarding school experiences. Namely, that time she had a crush on her English teacher, Ben Donovan. Nothing came of it, but her mother, Lily, falsely accused the teacher of assault and swept the whole thing under the rug. Or so she thought. But as early as Season 1, Vanessa lets slip a reference to Serena’s messy past. How she could have possibly known about the non-affair as an outsider is beyond us—and probably beyond the writers as well.

#13: Blair’s Mom Has Two Different Actresses

It’s usually noticeable when actresses change. Blair’s fashionable mother, Eleanor Waldorf, is a fashion designer and CEO of Waldorf Designs. In the pilot, she is portrayed by Florencia Lozano. After episode four, Lozano dropped out and was replaced by Margaret Colin. Eleanor plays a small role, all things considered, appearing in only 34 episodes, so the change in actress was easily missed by most viewers. Still, her relationship with Blair is strained, with Eleanor's own standards shown to have contributed towards Blair’s obsessive perfectionism. Whether Lozano or Colin, though, Eleanor is Eleanor.

#12: Too Much Thanksgiving

One thing “Gossip Girl” arguably loves more than gossip and drama is the holidays. The show’s Thanksgiving episodes are especially iconic, if very much frequent. In fact, Season 5 is the only season not to have one. Perhaps the most iconic Thanksgiving is Season 3’s “The Treasure of Serena Madre,” where Blair suspects her mother of keeping secrets, and Vanessa has a huge fight with her estranged mother. By contrast, there are only two Christmas episodes. Perhaps the drama among the scions of old American elites is more suited for the American holiday than Christmas cheer. That, and the fall aesthetics are gorgeous.

#11: Serena Gets Accepted Into Three Ivy League Schools

Now, this is a headscratcher. Between Blair and Serena, the former is by far the most academically inclined, Blair being the quintessentially anxious overachiever. By contrast, Serena is far from the most studious. She even misses the SAT, though that was caused by Georgina Sparks’ influence. So it’s a shock when Blair gets waitlisted at Yale while Serena gets accepted not only into Yale, but Columbia and Brown! Not only that, but Blair finds out her eventual transfer to Columbia is partially Chuck’s doing. Pretty rich girl privilege is one thing. A party girl who missed her SATs getting into three Ivys is another. Show, please.

#10: Nate’s Career

Okay, we understand that “Gossip Girl” doesn’t exactly depict a realistic teenage experience and that all the characters are super wealthy and privileged. But even within the world of the show, it seems pretty unrealistic that Nate was able to go from being an intern to becoming editor in chief of The Spectator in what seemed to be no time at all. Not to mention, when we see him in the series finale he’s inexplicably running for mayor? While we’re on the topic of unrealistic professional accomplishments, we have our doubts that Dan’s book would have ever been published, let alone make the New York Times bestseller list.

#9: Texting From the Inside

So the world of “Gossip Girl” may be slightly out of step with the world that us regular folks live in, but there are some basic rules that everyone has to follow, no matter how rich they are. In season four however, the diabolical Juliet is found to be plotting with her brother Ben, who is incarcerated at the time. And how were they communicating you ask? By text of course! Call us old fashioned, but even in the modern day we’re pretty sure prisoners aren’t allowed access to their cell phones.

#8: No Drinking Age

We’re not naive, we know that underage drinking happens, especially in countries like the US where the drinking age is 21. Of course, with their social statuses and trust fund accounts, the teens of “Gossip Girls” probably have to follow different rules than the rest of us, but they’re not totally immune to the law. Even when they’re still in high school, they’re shown drinking constantly, and never seem to have any restrictions whatsoever on procuring alcohol or getting into bars and clubs. Not to mention, Chuck actually buys a club while he’s still many years underage.

#7: Pretty Much Everything About Bart Bass

Viewers willingly suspend their disbelief about a lot of things while watching this drama-filled show, but everyone has their limits. Many plot points may seem unrealistic, but others leave you asking, “wait...what?” Bart Bass is often at the center of these head scratchers, whether it’s revealing that he was alive after several seasons of being presumed dead, or heartlessly trying to kill his own son. No matter how much money you have, faking your own death is near impossible, especially for such a prominent figure like himself.

#6: The Whole Charlie / Lola Thing

You’re going to have to bear with us on this one because as the seasons of “Gossip Girl” went on, the plotlines became more and more convoluted. In season four, Serena runs into a girl who she believes to be her cousin Charlie, and mentions that she hasn’t seen her since they were twelve. Later on though, when the real Charlie shows up and Ivy is proven to be an imposter, the actual Charlie says that she has been hidden from her extended family for her entire life. There’s no implication that Ivy has been working on this con since she was a kid, so this seems like a clear oversight.

#5: Lily & William’s Relationship

Serena’s father, doctor William van der Woodsen, doesn’t figure into the story until the show’s third season. When he does appear, it’s soon revealed that he is tricking his ex-wife Lily into believing she has cancer so that he can spend more time with her. Not only that, he’s actually giving her drugs to mimic symptoms of the disease. Despite this reveal, Lily and William end up together in the show’s series finale, with no real explanation for how she possibly managed to forgive him for such heinous actions. We’re just not buying this one.

#4: Is Chuck’s Mom Dead or Alive?

In the very first episode of “Gossip Girl”, Chuck casually mentions stealing medication from his mom while chatting with Nate. By season two however, he reveals to Dan in an uncharacteristically tender moment that his mom actually died while giving birth to him. And of course, because this is “Gossip Girl”, by season three we get a reveal that....she’s actually still alive! The thing is though, Chuck always thought she was dead so that line from the pilot must have been written before the story was well thought out.

#3: Lily & Rufus’s Son

In season two, it is revealed that when they were younger, Lily and Rufus had a child together. This is understandably groundbreaking for those around them, especially their respective children. But although much is made of this dramatic turn of events, the story eventually fizzles out after Scott Rosson actually enters their lives for a while in season three. His final appearance is at Lily and Rufus’s wedding and he is inexplicably never heard from again. He has only just met his parents for the first time, so this doesn’t really add up.

#2: College Dropouts

In the early seasons, much is made of the gang’s college applications, and in particular Blair’s aspirations to get into Yale. By the beginning of season three, our main characters are in their freshman year of college, though Blair ended up at NYU, much to her chagrin. Somehow though, as the show goes on, their scholastic pursuits seem to fall to the wayside in favor of a variety of other types of drama. By the final seasons, there seems to be almost no mention of them ever attending classes, but they also never say that anyone dropped out.

#1: Dan Being Gossip Girl

Though the show’s creators seem to have known Dan was Gossip Girl from the very beginning, there are so many times in the show’s run where this just doesn’t make any sense whatsoever. Starting with the pilot when he seems shocked to find out Serena is returning to town (when he allegedly wrote the post) to countless other instances when his reactions to Gossip Girl are completely inconsistent with the fact that he’s the one creating the content. He even acts like he doesn’t know who Olivia Burke is! Not to mention all the times when it was literally impossible for him to have written something. We really wish they had crafted this one better!

What other “Gossip Girl” plot holes drive you up the wall? Let us know in the comments!