Connivery, thievery, treachery, infidelity, romance, deceit. Are all of these…the characteristics of a Shakespearean play? Perhaps a soap opera? Not quite—try a mid-aughts show about a group of preppy high schoolers whose favorite accessories are thousand-dollar designer shoes and candy-colored leggings. I’m talking, of course, about the original Gossip Girl.
Though the show premiered when I was six, I thought I’d have a lot in common with the girls and boys of Constance Billard and St. Jude’s. I went to school in Manhattan, peddled through the city in a Catholic schoolgirl uniform, and traipsed down the streets of New York City with my crew like thousands of other high schoolers. Although I’m no Upper East Sider (scholarship-based commuter student here), and the closest museum steps to my West 13th alma mater were at the Whitney, I figured I’d at least see a few of my old haunts onscreen and feel waves of nostalgia. All city teens snacked on a slice of dollar pizza and Arizona Tea after school, no matter where they were from, right? Wrong, apparently!
Watching the likes of Blair Waldorf, Serena van der Woodsen, and the rest of New York’s fictional 1% was like entering a fever dream—a dramatic, high-stakes, plot-churning fever dream. But I buckled in, and what I can say for sure is that I was never, ever bored.
Here is everything I thought after watching Season 1 of Gossip Girl.
I Wasn’t Prepared for How Many Scenes Would Leave My Jaw on the Floor
Chuck Bass is nasty and petty. That’s the first thing I wrote down after cartoonishly gasping when Chuck—scorned and possibly heartbroken—revealed Blair’s almost-pregnancy to Gossip Girl. It was truly a flipped-switch moment: One second, Blair was dissing him, and the very next, he was furiously blasting her business via text on his Motorola Q.
Also, familiar as I thought I was with the casual plotting and scheming of the Constance Billard girls, I was not prepared for Georgina Sparks to enter the picture. When she cried on command to Dan, pulling that boyfriend-stalker story out of thin air; took the batteries out of his phone; and then hooked up with him, all so that Serena would go back to clubbing with her…I knew I hadn’t even seen the worst of the Upper East Side yet. Troubling as Georgina’s behavior was, however, that girl clearly had a gift. Perhaps she should have channeled it into a Hollywood career instead of just…teenage subterfuge?
Is 2000s Fashion Back? Or Have I Just Been Staring at Colored Leggings for Too Long?
I’ve probably seen more colored tights this month on the streets of New York than I have since the 2010s (honestly, I’ve seen red tights maybe three times), and the one thing I knew about Gossip Girl was that the show doubled down on that trend. It did not disappoint.
Once Blair showed up at Constance with red tights under her uniform, it was only a matter of time before everyone else in her clique had bright, candy-colored tights on themselves, even during Jenny’s reign. But perhaps the most unrealistic thing about the show—besides the fact that no one ever seems to get stuck in traffic, despite constantly taking taxis—was the lack of uniform checks.
If Lily and Rufus Never Make It, Maybe Dan and Serena Will…?
The parallels between the two van der Woodsen-Humphrey couples only became more apparent as the season went on. Not only were Serena’s mom and Dan’s dad each other’s first love, but both generations faced pressure to separate from an elitist van der Woodsen matriarch because the Humphreys don’t come from money.
But while Lily and Rufus were eventually driven apart, Serena and Dan held on—at least for a while. By the end of Season 1, they were broken up by Georgina, but I’m holding out hope that they can still make things work…
The Take-Down of Georgina Sparks Was One of the Season’s Most Satisfying Scenes
Complicated doesn’t even begin to describe the web of relationship statuses between Nate, Blair, Serena, and Chuck. Yet despite their history, all agree that anyone who messes with them will pay. When Serena confessed to Nate, Chuck, and Blair about that infamous night with Pete—and revealed Georgina’s twisted hand in it all—only to see the frenemies band together to take Georgina down, I honestly thought to myself, So this is the Upper East Side’s version of the Avengers!
And just to say it: Even with her diabolical savvy—and all the vengeful persistence of a woman scorned—there was no way Georgina was getting away with blackmailing Serena when the real mother of manipulation was involved…which is to say, Blair.
The Soundtrack to Every Episode’s Final Montage is Unmatched
From the emo stylings of Sum 41’s “With Me” soundtracking Blair and Chuck’s limo scene, to “The Ice Is Getting Thinner” by Death Cab for Cutie playing as the recently-split Dan and Serena had a last dance of sorts at Lily and Bart Bass’s wedding, nothing says Something’s about to go down quite like watching the Upper East Siders edited in slow-mo to ’00s hits.
Should I Feel Bad for the Upper East Siders? (Because I Do!)
The fictional uber-rich of New York have a lot of flaws—not to mention legal troubles. While I don’t think I’d ever want to go toe-to-toe with Blair Waldorf, or really be within Chuck Bass’s sights at all, I can’t deny that these teens have fearfully acute survival skills, even if they’re only deployed in social situations.
For instance, while I’m sure most would agree that falling out with your high school clique or skipping out on the secret school pool party isn’t the end of the world, for the teens of the Upper East Side, reputation is the only thing that matters. That’s not to say that I was rooting for Blair while she sabotaged top students’ SATs, or created hierarchical seating assignments on the steps of the Met—I wasn’t. But getting sucked into the Gossip Girl world means you know pseudo-first-hand how cut-throat life on the Upper East Side can be. It’s what made me sympathize with Jenny, who sold her sewing machine and stole a Valentino dress just to keep up appearances. I know she doesn’t have to do any of those things to prove herself worthy, but I understand why she felt so intently that she had no other choice. (And yes, one of those reasons was Blair.)
Finally, Who Is Gossip Girl? (I Already Have My Suspicions)
I’m not very far into the show, and Gossip Girl could very well be a character I haven’t met yet, but if I had to guess based on the cast of characters I do know...
I’m making the executive decision to rule out Blair and Serena; they’re just too prominently featured on Gossip Girl’s blog. I don’t think Serena would write about her own return to New York City after fleeing criminal charges; and Blair is a no because—while she is a manipulative mastermind—I get the feeling that she likes to take care of business in person, and revels in claiming responsibility once her target’s been had.
Maybe it’s Jenny—who, despite getting the backhand from the blog at times, is close enough to the inner circle of Upper East Siders to know all the tea. How does a freshman end up hanging out with juniors? Could it be because she knows exactly how the Constance/St. Jude’s animal kingdom operates?
But I also think that it could be Vanessa or Dan. Vanessa, because she could have easily blogged remotely from Vermont. Readers believe that Gossip Girl is a student, but she’s always getting tips, and could be piggybacking off of Dan’s information. Plus, she does get physically closer to the inner circle, and even begins work on a documentary about them via Dan—my final suspect.
I know—I know—that he’s Serena’s knight in shining armor, and one of the few characters with a non-questionable moral compass. But every time Dan speaks, I hear Penn Badgley’s homicidal stalker character Joe Goldberg from Netflix’s You. Though that’s biased and totally unrelated to Gossip Girl, Joe perfected the nice-guy act too!
Nevertheless, I have the nagging feeling that I’m only grazing the surface of the world that is the Upper East Side…and Brooklyn.
So, until next time? XOXO.
