I’ll never understand why I didn’t watch Gossip Girl until right now. Growing up, I was always a teen drama fanatic, quoting moments from Degrassi: The Next Generation with my friends, even going so far as to throw a Pretty Little Liars-themed party in college, taping “A messages” on my walls in blood red duct tape. Yet, despite my classmates arguing about Chuck and Blair as a couple, or agreeing on the ludicrousness behind the identity of Gossip Girl, I was never sucked in.

Flash forward to 2020, when quarantine started, and I began flying through shows like nobody’s business. Before I knew it, I found myself clicking on Gossip Girl when it become available on HBO Max. After learning that the series was getting a reboot, it felt like the perfect time to dive into the drama with these Upper East Siders.

Now, six seasons and 121 episodes later, I totally get the hype. While the gorgeous cast, lavish settings and melodramatic plotlines pulled me in, I realized that a big part of the fun was the ridiculousness of it all. In order to best enjoy Gossip Girl, I needed to fully embrace the story and all the subplots that weren’t 100 percent logical. And while I tried not to take things too seriously, there were still scenes so bizarre or unrealistic that I found myself actually scratching my head. So, I decided to compile a list of the top eight things from Gossip Girl that make absolutely no sense.

*Warning: Spoilers ahead*

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1. In this world, drinking laws just…don’t exist?

One of the most baffling elements of Gossip Girl is its embrace of underage drinking. These high schoolers frequent bars so often that we forget they’re technically not even old enough to vote. (Not only that, but these teens are in the habit of shaking up martinis instead of dumping Burnett’s vodka with whatever soda they can find into a red cup.) While their wealth might have provided them more access to alcohol, as well as the means to procure fake IDs, it’s still puzzling that they never encounter any obstacles to their drinking (except for one instance where they get caught drinking on school grounds). By the time they’re actually of drinking age, the viewer doesn’t even notice a difference. You’re telling me Jenny Humphrey (played by 14-year-old Taylor Momsen) wouldn’t even be questioned by a bouncer at a chic NYC club? I beg to differ.

2. Gossip Girl has tracking technology of the future

We all know the infamous Find My Friends app, used by Apple users everywhere to keep tabs on the location of their friends or exes. Interestingly enough, this same technology is available to track our favorite socialites—and it’s provided by Gossip Girl herself, well before the actual Find My iPhone program was introduced in 2010. It’s never really revealed just how this software works (or how it’s accessible on the T-Mobile Sidekicks and enV3s they carry around), but somehow, whenever a character is spotted, the Gossip Girl site is able to keep a live map of their location. If the FBI caught wind of this one, they would’ve surely been trying to buy it.

3. The Humphrey family is “poor,” but their loft is ginormous

The world of Gossip Girl is one where teens regularly take private limos to class and rent out convention centers for their birthday parties. So, when the privileged and wealthy Blair Waldorf refers to the Humphrey family as “poor,” I was kind of shocked. Of course, compared to the uber-wealthy families of Manhattan, the way of life for the Humphreys was quite different. But let’s not pretend like they weren’t living comfortably. Throughout the series, we spend a good amount of time in the Humphrey loft, where Dan, his sister Jenny and their father each got their own spacious rooms. Not only that, but the Brooklyn apartment featured cavernous ceilings, wide walkways, a large kitchen and gorgeous views of the city. If the Upper East Siders think this is some undesirable real estate, they should come take a look at the shoebox that I’ll soon be sharing with three other friends in Brooklyn.

4. Serena van der Woodsen gets into...YALE? and BROWN?!

Let me make sure I understand this correctly. After getting tangled in a group of heavy partiers, Serena van der Woodsen begins losing control and starts failing all of her classes. She spends a year away from school to collect herself and study “somewhere else.” She then gets someone else to impersonate her to take the SATs, gets arrested and starts a fight with her best friend at a Yale event. And still, she’s ultimately offered a spot at the prestigious New Haven, CT university, merely because she’s landed on the covers of a few local newspapers? Better yet, she DENIES that acceptance and then proceeds to never even show up to her first day at Brown University, where she was also accepted. I realize that wealth can play a heavy part in college admission, but if you could get away with all this and still be accepted into one of the top schools in the nation, then I would think we wouldn’t have this college admissions scandal on our hands…

5. Dan Humphrey falling for Blair Waldorf

The cast of Gossip Girl swap romantic partners almost every other episode. Fickle can’t even begin to describe these characters. However, while Gossip Girl was really stretching for some plotlines toward the end of its run, one of the most unfathomable details was Dan Humphrey’s romantic feelings toward Blair Waldorf. If a shared interest in old movies is really all it takes to fall in love, then I could’ve lingered at my local coffee shop and found my husband years ago. Despite the fact that Dan and Blair spend the first three seasons despising each other, Dan ultimately finds himself falling for the most calculating girl on the Upper East Side. And while I love a good “enemies to lovers” narrative, this one truly did not make any sense. Luckily, Miss Waldorf nips Dan’s romantic feelings in the bud pretty swiftly.

6. Vanessa publishing Dan’s book

I won’t pretend like I fully understand the nuances of publishing, but I think it’s fair to assume that Vanessa Abrams wouldn’t have had such an easy time publishing work that was not her own. At the end of season four, when she discovers the manuscript that Dan has written about his experience living amongst Manhattan’s social scene, she takes it to a publisher and runs away to Spain, before sending Dan the money she received for the book. While many people spend years trying to get a publisher to print their first work, this teenager’s writing was just so gripping that the editor was willing to take it from someone who had stolen it. Meanwhile, when Dan discovers that his manuscript was sold without his permission, he gets over the whole situation far too quickly for anyone to believe.

7. Lily van der Woodsen sending a man to prison

No character on this show was more mystifying than Lily van der Woodsen (portrayed by Kelly Rutherford). Even though she is so obviously in love with Rufus Humphrey (and admits it to him on her wedding day!), she still decides to marry Bart Bass. Even though she’s put on parole, she decides to throw a party during her house arrest. But, while she makes some very questionable decisions, perhaps her greatest is the framing of an innocent man as a sex offender. When Serena finds out that her mother sent her former teacher to prison (in an effort to help protect her daughter’s reputation), she is, rightfully, upset. As were we. Luckily, the van der Woodsens work to get the man released. Why Lily made the decision in the first place is a mystery I’ll never solve.

8. Dan being revealed as Gossip Girl

So much has been discussed about the unveiling of Dan Humphrey as Gossip Girl that I’m not even sure what’s left to say. Writers have tracked all the ways in which Dan couldn’t have been Gossip Girl, while also unveiling clues that show how it made sense. The show’s screenwriters even revealed that Dan wasn’t originally meant to be Gossip Girl, while the series’ cast has expressed their confusion at the reveal, with Penn Badgley himself admitting that he was unaware of the twist. While it’s almost impossible to believe that Dan could have been secretly maintaining the gossip site, while also getting high marks in school, writing a bestselling novel and taking care of a baby that he thought was his own, I’ve gotta give props to the writers for giving us an ending we definitely did not see coming.

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