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The 13 Most Unbelievable Things That Happened on Gossip Girl

Penn Badgley. Photo: The CW

A decade ago, the CW launched Gossip Girl, a sudsy teen drama about boarding school kids with Birkins and drug habits. Everyone was obsessed with the show despite it being so ludicrously plotted that it spawned its very own Reality Index to score its every move. In honor of the show’s tenth anniversary, here are the most absurd moments we witnessed in the lives of Serena, Blair, Nate, Chuck, Dan, and (ugh!) Jenny.

Gossip Girl’s Identity
Let’s get this out of the way first: There is no way that Dan Humphrey could have been the show’s titular blogger. It’s just not possible. Even actor Penn Badgley thinks it’s bonkers. What’s even more frustrating is that after the series finale, executive producer Stephanie Savage said that Dan was supposed to be Gossip Girl all along. In fact, they actually reedited the pilot when test audiences figured out the secret too quickly.

Let’s just look at that pilot. In it, Dan reads a post on Gossip Girl that Serena is looking for a date to the Masked Ball. When he comes upon this news, he is shocked — shocked! — and decides to ditch Vanessa to take Serena. If he just wrote the post, why did he need to read it? It’s like someone else told M. Night Shyamalan that the creepy kid sees dead people and he bugged out!

Throughout the course of the series, Gossip Girl reveals — against Dan’s wishes — things like his reunion with Serena, the existence of Lily and Rufus’s love child, Serena’s drug overdose, and his sister losing her virginity and being a drug dealer. He also uses Gossip Girl to help him find Jenny when she disappears to throw a guerrilla fashion show. If he knew where she was all along, why even bother using the internet?

There’s a cottage industry of blog posts pointing out all the inconsistencies in this revelation. But the most glaring happened in season five, when Blair is about to marry stupid prince Louis. In the middle of the ceremony, when Dan is standing on the altar as a best man, Gossip Girl publishes a post containing a video of Blair telling Chuck that she still loves him, which was recorded immediately before she walked down the aisle. Not only was it physically impossible for him to capture that video, it was also impossible for him to write and publish the post while in the middle of a very public event. Is he such a good typist that he penned the whole thing with one hand while his phone rested in his blazer pocket?

Serena Getting Drugged Twice
If someone gets a drug slipped in their drink at a club once, shame on the person who put it there. If someone gets a drug slipped in their drink at a club twice, shame on the writers for not coming up with a better plot. Seriously, Serena got dosed in season one by Georgina Sparks and again in season four by Juliet Sharp. Couldn’t they think of something better?

Dan’s Story in The New Yorker
Sure, Lonely Boy might be a very talented writer. Sure, there are some literary magazines that will publish young writers. However, Jonathan Franzen can’t even get all of his stories into The New Yorker. The show expected us to believe that the pinnacle of literary publishing in America would devote some of its pages to an unknown high-school junior whose best friend sent in his story as a blind submission?

Jenny’s Fashion Career
Why would Eleanor Waldorf, the heiress behind a million-dollar fashion business, put everything in the hands of a 16-year-old intern with way too much eyeliner? Just because Jenny goes to school with her daughter? No one thought to ask how this raven-eyed moppet was putting in so many hours when she was supposed to be in study hall?

Chuck Bass Owning a Bar
In season three, Chuck opened a rip-off of The Box called Victoria. The kid just graduated high school and was ostensibly 18 years old. Do you think for a second that New York City would give a liquor license to a kid who isn’t even legally old enough to drink?

Nate Archibald Running The Spectator
Yes, this was the era when Jared Kushner ran The Observer, but he “went to Harvard.” When Nate was put in charge of this New York newspaper, no one believed that he was smart enough to actually, you know, read a newspaper.

Rufus and Lily’s Love Child Dating Vanessa
That a socialite and her Seven Mary Three–esque ’90s rocker boyfriend would give up their child for adoption isn’t unbelievable. What no one could buy, however, was that their love child would blow into town and decide to date Vanessa. Seriously, what did he love about that girl? Her caveman hair? Her petulant whining? The smell of burned espresso forever baked into her fingers? Also, after he revealed his identity, he disappeared never to be heard from again, like the clap after seven days of Cipro.

Everything About Vanessa
While we’re at it, it’s impossible to believe that anyone would be friends with this self-important, overly sincere, constantly meddling barista from Brooklyn.

Bart Bass Coming Back From the Dead
By the time season five rolled around, everyone had hooked up with everyone else and the show was out of twists and shocks. So when Bart Bass returned to torture his son Chuck, we all just rolled our eyes and went along with it. By the time he was hanging from the side of a building and Chuck let him plummet to his death, though, nobody bought it.

Georgina Sparks Finding Jesus
Georgina Sparks was the best character ever on this show. Don’t @ me. Actually, go ahead and @ me because I will defend her to the death, like Khaleesi pulling a giant arrow out of one of her dragons. Anyway, the one problem with Georgina happened in season two, when she suddenly found God and wouldn’t join up with Chuck in some expert scheming. We all knew this would last about as long as Serena’s sobriety.

Ivy Dickens Being in the Will
Okay, let’s see if we can remember this correctly: Ivy Dickens was an actress hired by Serena’s aunt Carol to play Charlie Rhoads, Serena’s long-lost cousin, so that Carol could get access to Charlie’s trust fund. (Like no one would remember that Charlie’s, like, whole face had suddenly changed.) After the ruse was revealed, Ivy stuck around for two more seasons — apparently just long enough for CeCe, Serena’s manipulative grandmother, to leave Ivy her entire estate. To a complete stranger. Don’t worry, Lily and Carol made sure that didn’t happen without even stepping into a probate court. Which was equally unbelievable.

Dan and Serena Sleeping With Their Teachers
Yes, Dan’s whole thing with Ms. Carr was creepy in a Mary Kay Letourneau kind of way and it was, you know, illegal. But being “hot for teacher” is nothing new. Things got really crazy when Serena started an affair with her old teacher Ben. You know, the one who was sent to prison for having feelings for Serena when he was her English teacher. And just so things don’t get too weird, Serena also dated Ben’s cousin Colin when he was her teacher at Columbia. I mean, what was this show even about?

Dan and Blair Getting It On

The 13 Most Unbelievable Things That Happened on Gossip Girl