We Found The Biggest Plot Hole In The Gossip Girl Storyline

Becca Van Sambeck
Becca is a recent Fordham grad, a former German beer hall girl, and a new Brooklyn resident who used to read the dictionary for fun as a kid. She has only gotten slightly less lame since then. She loves pugs, chicken fingers, reading and Game of Thrones.

No one in their right mind would ever pretend Gossip Girl was a paragon of realism. Most people’s high school experiences don’t include sleeping with your ex-boyfriend’s best friend in a limo after doing a striptease at a speakeasy, so we know we’re not watching Gossip Girl for documentary-level realness. Still, there was one thing upon rewatching after years of living in New York that stretched the limits of plausibility for me.

Was it all the times Dan, who’s supposedly Gossip Girl himself the whole time, sat in a room alone looking shocked and horrified at the scandalous headlines he created, as if he was merely being possessed by some incredibly bitchy, pun-loving demon? Or how Rufus and Lily discovered they had a secret love child that they so desperately wanted to know, only to meet him, send him off and never give a single thought to his existence again?

No, clearly the most glaring flaw in this show about New York City is its insistence on pretending that the Upper East Side is walking distance from Brooklyn.

Look, I live in Brooklyn now and I can’t even get friends who live in SoHo to come over for dinner. I know plenty of Brooklynites who have admitted someone living above midtown is a dating deal breaker. Are we really expected to believe that Dan just casually hops off to Williamsburg during his lunch break from his Upper East Side school? Because that’s exactly what he does, just flits like a carefree butterfly down to Vanessa’s cafe an hour away. The time to get down there would take longer than your typical lunch break. Dan is the guy who loves school so much he thinks its acceptable to date his teacher. He’s not going to ditch three hours of school for Vanessa.

Or, of course, there was the beautiful Season 1 Christmas episode where Rufus decides he must declare his love to Lily NOW. This is a lovely sentiment, you’ll probably think as he strides defiantly into the street in just a threadbare jacket. Surely he’s about to flag down a cab, right? Nope, no, he’s walking from Brooklyn to the Upper East Side on a snowy December night. That is literally hours of walking in the freezing cold, dressed like the little matchstick girl. Leo in The Revenant had an easier journey, for God’s sake.

But what happens with the most perplexing regularity is how the Humphreys happen to casually head out from their Williamsburg loft to the van der Woodsens’ apartment for breakfast before school.

This is ridiculous on so many levels. Jenny Humphrey is a teenage girl. Let’s work backwards to see how early she would have to get up to make it to the van der Woodsen’s home for a legit breakfast before school.

7:30 a.m.: Everyone knows high schools bizarrely start at the crack of dawn, and while these kids may be blessed with perfect hair and boatloads of money, they’re still not exempt from a normal school start time.

7:10 a.m.: The van der Woodsens are lodging at the Palace Hotel, on 50th and Madison. I Googled the address of the high school they supposedly attended, and while fake, it also has a fake address (719 E 82nd Street, so east it’s actually in the East River.) According to Google Maps, this is a 20 minute drive. Therefore, the kids are probably piling into the Rolls Royce to be chauffeured to the middle of the East River around 7:10 in the morning.

6:40 a.m.: The van der Woodsens always have a giant spread of toasts and jams and muffins and fruit all assorted out on the table, despite the fact that there’s no way Serena or Jenny have dared to eat a muffin in years. Still, if they’re going to all this trouble to attend a big ass breakfast at their dad’s girlfriend’s place, it’s safe to say they’re trying to be there for at least a half hour.

6:00 a.m.: While we have a concrete address for the van der Woodsens, we aren’t gifted with such a clear idea of where the Humphreys live. We’re told over and over again that they live in Williamsburg, so I just typed in Williamsburg into Google Maps. The results I got back were equally vague, with Google Maps telling me it would take anywhere between 20 to 40 minutes to get to the Palace from their hypothetical loft. We know they can’t risk being late and cutting into their time pretending to eat carbs, so they’re definitely not pushing their luck, and are thus leaving 40 minutes early.

PLUS, isn’t Dan always whining about how poor he and his family are? How he can’t date Serena because she has money and he’s just a poor pauper, with nothing to offer? They’ve never mentioned owning a car. Thus, we’re supposed to believe that they’re regularly cabbing it up from Brooklyn to Midtown, in a time before Uber pool? Maybe they’re taking the subway over, but, while more cost-efficient, will definitely cost them the time with Lily and Serena that they’re clearly so desperate for.

4:30 a.m.: Jenny Humphrey has a shit ton of hair and even more eye makeup. This is not a girl who can even pretend that she just woke up like this. One would think that wearing a uniform would cut out all the minutes spent angsting over what to wear, but not at this school, where everyone’s always dressing up their uniforms with headbands and ribbons and blazers and knee socks. Jenny, as established early on, cares about FASHION. It’s her LIFE. She’s not sleeping in until the last minute, she’s getting up an hour and a half early to get Raccoon Eyes Perfect.

If this show was real, Jenny would be getting up literally before the sun (if we’re being generous and pretending that all the roadblocks in the morning don’t exist) just to have breakfast with the bitch who foiled her plan to go all Parent-Trap with her real mom and dad.

No. Jenny is up hours into the night, sewing Hot Topic knock-off jumpers and reading Gossip Girl and plotting ways to ruin Blair Wardolf’s night. She’s not waking up at 4:30 every morning to prance off into school. If this is true, her trademark dark eye makeup could just be her genuine undereye circles from those sleepless nights.

Gossip Girl, look, I know you’re a show about drama and dresses and romance. I can believe that Serena killed a guy and it was all NBD, I can believe that Blair dated a British lord who was screwing his stepmom who was also dating Blair’s high school ex, I can believe that Nate, literally the human equivalent of a wink, became a successful and respected newspaper tycoon.

But I just can’t buy that these people can cross town so much in a time before Ubers. Sorry.

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