The 20 Best Episodes of Gossip Girl

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Gossip Girl is returning to HBO Max with a new reboot premiering July 8, featuring 10 juicy hour-long episodes featuring the original eponymous narrator Kristen Bell.

The reboot will take place eight years after the final surprising twist ending that revealed the true identity of Gossip Girl. We’ve been clued in on how stylish–and cool–the new characters are, but don’t know too many details about the new reboot.

As we wait for the premiere, we’re taking a look back on the six original seasons, in all its high-society New York glory. Here are the best episodes of Gossip Girl, to catch up on while you wait for the remake.

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Leighton Meester as Blair Waldorf and Blake Lively as Serena Van Der Woodsen in season one of Gossip Girl.Photo: © CW Network / Courtesy Everett Collection

“The Pilot,” Season 1, Episode 1

Of course, the very first episode of Gossip Girl has to be on this list. It’s the introduction to all of the characters and their basic plotlines throughout the six seasons: Serena, who bites her lower lip and falls for guys within five minutes; Blair, who pretty much hates Serena but still acts like her best friend; Daniel/Lonely Boy (imagine that being your nickname, yikes), who’s creepy, stares longingly in the background, and is low-key miserable; Nate, who doesn’t really serve much of a purpose but is beautiful; Chuck, an odd 50-year-old in a 17-year-old body (he eventually does undergo a rebrand); and Jenny, who longs for nothing more than to be a Manhattan elite.

It also introduces us to the fact that these sophomores in high school attend parties on weekdays far more than anyone else does, and that their original casting for Eleanor Waldorf was abysmal.

“Victor/Victrola,” Season 1, Episode 7

The episode where Chuck and Blair’s romance officially began. Bart Bass is interested in buying a burlesque club, so he sends his sophomore-in-highschool son to go check it out. While he’s there, Blair gets over her breakup with Nate by letting it all go on the burlesque stage–and Chuck’s into it. Then Blair is very into Chuck being into it. So into it that she loses her virginity to him in the back of his limo. Very different experiences from when I was a sophomore in high school but an episode to remember.

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“Blair Waldorf Must Pie,” Season 1, Episode 9

Our introduction to the best of Gossip Girl: the Thanksgiving episodes. The introductory Thanksgiving episode has a little bit of everything: a glimpse at just how long Dan has been obsessed with his current girlfriend, Serena; flashbacks to happier times at the Waldorf family before Blair’s dad left her mom for a hot male model named Roman; the fact that Lily Van der Woodsen and Rufus Humphrey are basically the adult version of Dan/Serena and that they had a full-blown love story; and the fact that despite having a full spread of food on almost every table in this show, the characters never eat any of it.

“Desperately Seeking Serena,” Season 1, Episode 15

It’s springtime in the Upper East Side which means it’s time for us to all be introduced to the one and only Georgina Sparks. This episode really highlights what we all love about this show. It has amazing outfits and everyone’s having cosmopolitans in bars on a school night even though they’re supposed to be in what, the 10th grade? 

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