Gossip Girl Moments You Just Can't Stop Thinking About
There are simply too many to choose from...
Hello Upper East Siders, another Thanksgiving has come and gone. And what am I most thankful for? The truth.
Amen, Gossip Girl! But what we’re most thankful for is all of you.
One of the things we’ve heard again and again since we started this silly little newsletter over six months (!) ago is “wow, I can’t believe y’all are still doing all of that every week.” And honestly, neither can we! A consistent writing routine outside the parameters of a paycheck is like one of those goals you write in a planner on New Year’s Day and tend to diligently for about three weeks before life gets in the way. But seeing our open rate stay consistently high every week and hearing all of your comments and opinions (yes, the praise is nice… we’re writers!) has kept us honest and at least somewhat regimented (when exactly does this newsletter drop every week? That’s a secret we’ll never tell because we don’t even know.1) Writing about our favorite topic every week for all our friends and colleagues and new friends (if you subscribe, you are our friend and you simply have to face the reality of all that entails… which is mostly just reading all of these very long parentheticals we insert into every paragraph) has been the highlight of our year. And so for you YWSWers, we give all our thanks.
Anyway, we’ve reached the end of The Five Days of Gossip Girl and, as promised, here are some of our readers, friends, fellow Substackers and our favorite Gossip Girl moments.
One line reading that I think is absolutely perfect is Chuck thinking his father's last words might have been "why do you wear so much purple?" Anytime I see someone wearing purple, I hear Chuck Bass in my head. — Lizzie Logan of Lizzie Logan Is A Genius
Jenny googling “cancer.” — Maria Robins-Sommerville of Is This Available?
The one plotline that sticks with me for its sheer absurdity is Blair's pact with God to marry Louis and keep Chuck alive. There's a moment when, after she thinks she can be with Chuck, she watches him almost get hit by a car and thinks it's a warning from God. The writers were so desperate to prolong the will they won't they for as long as possible that they shoe-horned in a very selfish person suddenly becoming a religious altruist. I remember laughing out loud, and continued laughing through GG's disastrous spiral to its conclusion. Perfect show. 10/10. — Meg Walter, co-host of Hive Mind
As a TeenDramaWhore who ships both Derena AND Serenate, it was hard to make a final decision here — do I go with something heartwrenching, like Dan and Serena's elevator breakup (which I recently wrote about for my day job), or something heart-bursting like Serena finding out Nate loved her? Ultimately, I decided on something sexy: Serenate's berry hot time with some strawberries. It was *chef's kiss* — Shari Weiss of TeenDramaWhore (Twitter: @sizzlemaker, Instagram/Threads: @teendramawhore)
I have been thinking a lot lately about "three words / eight letters" because of Iron Flame, the sequel to Fourth Wing that just came out. No spoilers — I'm only halfway through — but Xaden and Violet are having a very similar fight. But in general... the Hilary Duff threesome. — Julia Glum (Twitter: @SuperJulia)
I'm forever thinking about the VitaminWater brand activation disguised as a white party in the Hamptons during the first episode of the second season. It's campy, shamelessly excessive, and pairs a top tier Blair look with an iconic Lady Gaga needledrop — what more can you ask for? — Lola Kolade of Brain Rot
I spent a good chunk of the early pandemic thinking about Gossip Girl fashion, so omg moments are inextricably linked with omg what is she wearing? One look I will never stop thinking about: Blair's eighteenth birthday party dress. The ruffles! The open back! And of course, it coordinates perfectly with Serena's cream-and-black dress. — Chrisinda Lynch of Clean Takes on Soapy Fashion
Jenny saying “I’m ya sista, it’s what I dew!” — Mary Beth Barone and Benito Skinner, probably.
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Serena throwing away her phone instead of deleting Blair's number?? And then in the next episode it's never addressed and she has a new phone. — Nabila A
I clearly woke up (and went to sleep) thinking about the plight of Eric van der Woodsen because I can’t stop thinking about when little J had her minions dump food (maybe a milkshake?) on Eric for sitting higher on the steps than her. Or when Georgina outs Eric to Lily at dinner and thinks she is doing everyone a favor?? Lily’s overly dramatic and wholly unsupportive response kept the punches coming. But when Blair shows up with Georgina’s parents and had seemingly convinced them to send Georgina away for help also sticks out and I guess should provide some resolve. — Brandon S
Chuck and Blair watching their lookalikes hitting it off at that one dance was a fun watch. — Anja L.
Jenny moving out in high school after she and Rufus fought so she could do fashion. (By Rachel and Mallika’s count this happened at least 10 times) — Ray N
Rufus & Lily’s love child who got an episode of screen time, that made me so mad they never brought him back!! Also the drama with Chuck's mom? Feel like it was so hyped up & the payoff was eh. Nate existing in the later seasons just to hook up with beautiful women, contributing nothing to the plot IMO. Also Bart bass funeral ep was so good just for him to have faked his death in the end? So weird. — Jenny K
I will never stop thinking about Hilary Duff’s Gossip Girl appearance in general but more specifically her performance during a supposed modern retelling of Snow White using the music of Lady Gaga. That is absolutely something that would happen at NYU Tisch so that’s not what makes it ridiculous. But the thing about writing the lyrics “it's complicated and stupid, got my ass squeezed by sexy Cupid” is Lady Gaga did not intend for them to be sung basically a cappella by Hilary Duff to Dan Humphrey while he’s in a fedora and they’re dealing with the aftermath of their awkward threesome. I absolutely love Hilary’s dramatic singing entrance from the back of the room only for her to give basically nothing and walk out. The girl knows how to get her money and go and for that, I must respect her. — Mallika
About two years ago, a couple of friends and I went to a party at Baby’s Alright for the premiere of Penn Badgley’s new podcast “Podcrushed,” and as was promised to us in the invite, Penn and his co-hosts got on stage to introduce the new podcast all about middle school trauma, and then afterwards there was a dance party with early aughts throwbacks. We weren’t sure if Penn would actually stick around and party with us, but sure enough his wife (who is Jessa from Girls’ sister if you didn’t already know) dragged him to the middle of the dance floor. I can’t tell you how surreal it was to be dancing to Fergie’s “Glamorous” with Dan Humphrey jumping up and down just a meter behind me. It was made even more surreal when a few days later, I resumed my annual Gossip Girl rewatch and an a cappella rendition of “Glamorous” crooned over shots of all our favorite Upper East Siders getting ready for another episode full of drama in season one. Even before I had that incredible Penn Badgley encounter, I still considered this to be one of the show’s best openers. Jenny’s school choir’s rendition gives the very on-brand pop song a hollow, almost menacing feel, which is a perfect setup for what’s to come. — Rachel
And that’s a WRAP on us using this reference in 2023.