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These Are the Best ‘Gossip Girl’ Episodes You Have To Watch


Hey Upper East Siders, word is Gossip Girl is leaving Netflix Canada on December 31. Which can only mean one thing: there’s a GG marathon in your future. The hit CW show, which ran from 2007 to 2012, gave us so much; from *amazing* style and questionable underage partying to sweeping views of New York City and iconic Thanksgiving episodes, the world of Gossip Girl truly had it all. Not *entirely* prepared to hunker down and power through six seasons of wacky, titillating, completely out-of-touch TV in two short weeks? We don’t blame you. With some of the earlier seasons of the show boasting up to 25 (!!) episodes, trying to make it through the entire series, whether for the first or the fifth time, is a big time commitment. Luckily, we have you covered. Looking to dive into the Romeo and Juliet-esque world of Dan Humphrey, Serena van der Woodsen and NYC’s elite? Here are the episodes you need to watch. (Warning: some spoilers ahead.)

“The Pilot” (Season 1, Episode 1)

Of course, in order to get a handle on any new series it’s imperative to watch the pilot episode, no matter how cringe-worthy the quality and acting may be in hindsight (looking at you, Scandal). And the same rule applies for GG’s inaugural episode. In the show’s first episode, viewers are introduced to all of the major players, most importantly the Humphrey and van der Woodsen families as well as queen Blair Waldorf (played by Leighton Meester) and her main men Chuck Bass (played by Ed Westwick) and Nate Archibald (played by the always hot Chace Crawford). Kicking off with socialite Serena van der Woodsen’s (played by Blake Lively) return to New York after leaving the year prior under mysterious circumstances (semi-spoiler: she thought she accidentally killed a man), this episode sets up many of the themes that the series will come to be known for, including: class conflict, rivalry, underage drinking and sex, and Dan Humphrey’s (played by Penn Badgley) obsession with Serena.

“Hi, Society” (Season 1, Episode 10)

Almost halfway into the first season of the show, the next must-watch episode serves a heavy dose of what GG does best—insanely un-relatable and unlikely displays of grandeur. In this episode, Gossip Girl takes us into debutante season, with Blair and Serena ready to make their debut into society. A lot goes on in this episode, but what makes it worth a watch are the advances in various romantic relationships. Blair and Nate *finally* have sex for the first time (albeit after Blair’s already slept with his BFF Chuck Bass, unbeknownst to Nate, of course), fans get a bit more of a backstory into Lily van der Woodsen and Rufus Humphrey’s past (as in Lily’s mom forbid them from being together), and after initially being thwarted by Serena’s grandma, who doesn’t approve of Dan and his standing in society, Serena and Dan cement their love for each other when Lonely Boy shows up at cotillion and literally sweeps Serena off her feet in a scene that made my 15-year-old self scream with glee.

Plus, Lily and Dan share a lot of tender moments in this episode, which is just really nice and a small insight into how kind and warm Mrs. van der Woodsen could actually be.

“Desperately Seeking Serena” (Season 1, Episode 15)

For fans of the show, this episode is the real first glance into what Serena was supposedly like before she returned to Manhattan as a reformed former party girl. In this episode, Serena’s old frenemy Georgina Sparks (played by Michelle Trachtenberg) returns to the UES as everyone is furiously studying for SATs and essentially derails S’s entire good girl schtick, coercing her into drinking and even drugging her the night before the big exam. This causes a rift between Serena and Dan, with Serena refusing to let Dan know what’s going on or why she’s so beholden to this old friend. (Again, it’s because she thought she killed someone which we learn was another Georgina set-up.) This episode introduces one of D and S’s major relationship problems: communication issues and a lack of understanding each other’s respective worlds.

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“Never Been Marcused” (Season 2, Episode 2) 

It’s summer and everyone’s in the Hamptons! After being scorned by Chuck at the end of season 1, Blair is back from Europe with a fancy pants boyfriend and Nate is having an affair with an older, married woman (who we later find out is Blair’s boyfriend’s step-mom). This episode is bonkers, specifically because Nate and his older female friend are reported to have met in a book club. Because 17-year-old guys who summer in the Hamptons totally join bookclubs with middle-aged moms. This storyline serves as the first of many for Nate that involve an older woman, but it’s by far the most interesting. And it’s just so fun to see everyone tanned and sporting their best summer attire! This episode also marks the first of many relationship reunions between Dan and Serena. (It’s definitely their most tanned reunion on record.)

“Pret-A-Poor-J” (Season 2, Episode 8) 

Enter: Dark Jenny. As any Gossip Girl fan knows, the character of Jenny Humphrey (played by Taylor Momsen) goes from Brooklyn’s good girl to pretty much the worst character on the show in record time. There are *several* instances throughout the series when Jenny goes over to the dark side, falling victim to the allure of the Upper East Side and the power that comes with being on top. In season 1, we see Little J become a mean girl in her quest to get in with Blair and her popular crew on the steps of the Met gala. And after a summer of de-programming, she’s back to her old self and ready to devote herself to her passion for fashion design. But it’s not long before Jenny starts to go off course again, quitting her prestigious internship with Blair’s fashion designer mother (which was actually kind of justified—her designs were being ripped off), and going out on her own. While this iteration of J doesn’t start off bad, per se—Jenny just wants to start her design career!—leaving home and being rude AF to Rufus, moving in with a hectic model she barely knows and quitting school, all so she can start a fashion line at 15—is pretty bratty and chaotic.

By the way, you’ll know Jenny has gone to the dark side because of all the heavy eyeliner and mullet hair she’s sporting.

“The Goodbye Gossip Girl” (Season 2, Episode 25) 

In the second season’s finale episode, everyone is graduating. Serena takes this opportunity to not only wear a graduation cap tassel in her hair, but also to decide that Gossip Girl has to go down. The result? GG releases dirt on some of the biggest moments from that year, including Dan sleeping with a teacher and Blair sleeping with Chuck’s uncle (info that was released *just* as Blair and Chuck were about to get together). It’s essentially a recap on any scandal from the season that you need to know. The highlights of this episode include Lily and Rufus *finally* getting engaged, and Chuck *finally* telling Blair that he loves her. It’s a surprisingly sweet end to a season of discord between the two over those three little words.

“The Freshmen” (Season 3, Episode 2)

Serena and co. are off to university! The second episode of the third season sets up the new dynamics for the show–and our characters’ lives—because they aren’t at Constance anymore. In this episode, it becomes increasingly clear that while Blair may have been the top dog in high school, people at New York University could care less about sushi parties, limos to Butter and her incessant scheming. They just want a fun rooftop kegger thrown by Georgina Sparks and to watch Vanessa Abrams’s (played by Jessica Szohr) indie doc. This is a great episode because, for once, the roles are reversed, with Dan finally being the popular one. We get to see Blair try to weasel her way to the top (unsuccessfully), and realize that things in university won’t be the same as they were in high school (and they definitely shouldn’t be). This episode is also A+ for the very fact that it’s one of few in the series where we get to see Chuck and Blair together and actually happy (if only for a brief period of time), and it marks the demise of Blair’s penchant for headbands.

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“They Shoot Humphreys, Don’t They?” (Season 3, Episode 9)

This episode is defined by two things: Jenny once again going over to the dark side and trying to be queen bee of the entire UES (only this time rocking really bad extensions) and a threesome between Dan, Vanessa and Dan’s new famous actor girlfriend Olivia (played by Hilary Duff). Yes, you read that correctly: Lizzie McGuire has a threesome in this episode!!! The fact that this occurs, as well as the musical build-up to the moment when the trio decide to take the plunge (featuring a confusing sensual cover of T.I.’s “Whatever You Like”), are 100% the only reason to watch this episode and only this episode in season 3. (Oh, and also, Dan and his BFF Vanessa’s ongoing sexual and romantic tension is *finally* addressed.)

In case you were wondering, at the time in 2009, this was a scandal with a capital S, with the Parents Television Council boycotting the episode and calling for it to be removed. That’s *so* Gossip Girl!

“The Treasure of Serene Madre” (Season 3, Episode 11)

If Gossip Girl is known for one thing besides headbands, it’s their Thanksgiving episodes. A staple of the series, it’s always a guarantee that Thanksgiving on the UES will be filled with pie and tons of drama. And the season 3 Thanksgiving episode is no exception. Set to Imogen Heap’s “What’cha Say,” this scene is peak GG, highlighting all the tension between different individuals in under three minutes. Blair thinks her mom is secretly pregnant, Jenny finds out her step-brother Eric sabotaged her cotillion, it’s revealed that Serena’s having an affair with Nate’s married congressman cousin, Vanessa and her absent mom get into it over who has the right to give parenting advice, and CeCe van der Woodsen—Lily’s mom—is just…there. Always stirring the pot.

Watching everyone hash out their ire and storm away from the table is like a dramatic game of musical chairs, and it’s GG at its best.

“The Debarted” (Season 3, Episode 12)

It’s the one year anniversary of the death of Bart Bass, Chuck’s father (although *spoiler alert* he faked his death), and everything is hectic in everyone’s world. After running away with her married BF, Tripp van der Bilt, Serena and said boyfriend get into a car crash, with Tripp calling 911 and leaving the scene. In other news, Rufus learns that Lily may have cheated on him with her ex, Dan confesses his love for Vanessa (it’s not reciprocated) and Chuck thinks he sees his dead mother at his father’s grave. Come for Nate punching his cousin out and the start of his relationship with Serena, and stay for one of a few very rare scenes of Blair and Chuck supporting each other.

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“Double Identity” (Season 4, Episode 2)

After being mugged in Paris at the end of the last season, Chuck wakes up a new man, having been saved by a Parisian woman named Eva with whom he instantly falls in love. Elsewhere in Paris, Serena and Blair are trying to figure out their own romantic woes, with Serena set to head back to the U.S. and trying to decide between Dan and Nate, who’ve both shown interest in her. Oh, and Dan reportedly has a son Milo, after Georgina Sparks showed up pregnant later in the third season. (ICYMI, Dan and Georgina briefly hooked up at the beginning of season 3, and it doesn’t take a genius to figure out that Milo isn’t *actually* Dan’s son, something Rufus Humphrey figures out towards the end of this episode.)

But the main reason to watch this episode is the main reason to watch this entire show, TBQH: Chuck and Blair. Having screwed Blair over for most of the series, finding himself in Paris with no ID, Chuck plans to reinvent himself as “a person someone could love.” Meeting Chuck at the train station in Paris, Blair urges him to come home, saying that although she doesn’t love him anymore, “it wouldn’t be my world without you in it.”

This scene is probably one of the most honest and frank discussions the couple has in the entirety of the series; and it’s SO clear that they still love each other but are trying to do what they think is best. This episode marks the start of more than an entire season of distance between the pair, but at least they’ll always have Paris (and that gorgeous red gown).

“Father and the Bride” (Season 5, Episode 12)

Blair’s wedding day is here! Yes, if you’re just catching up on season 5 now, during the front half of this season, Blair has been wined and dined, fallen in love (kind of ) and fallen pregnant by Prince Louis of Monaco. Long story short: Queen B knows she still loves Chuck and that he’s the love of her life (what’s frickin’ new?), but thinks she can be happy with Prince Louis.

That *is* until her wedding day when bad girl Georgina records Blair confessing her love for Chuck and then plays it for Blair’s future hubby. And how does he react? By going through with the marriage, only to tell Blair—while on the dance floor during their first dance as husband and wife—that their marriage will be entirely for show. Uh-oh B, what will you do? (TBH not much, aside from getting divorced and briefly dating Dan, a storyline no one needed.)

“New York, I Love You XOXO” (Season 6, Episode 10)

Potentially the most divisive episode of the show’s run is the series finale. After six seasons of ups and downs, the infamous Gossip Girl is *finally* revealed, and it’s not who anyone expected. Whether or not you’re happy with who the show ultimately chose is beside the point (plus, the cast themselves clearly hate the decision, which is honestly the best), because the final episode gives us tons of great closure for our favourite characters. This includes the marriage of *SPOILER ALERT* Blair and Chuck in Central Park (shortly before Chuck is arrested on suspicion of invasion of privacy and slander, because obviously). Trust me, by the end of this watch, somehow these two will have become the couple you’re *actually* rooting for throughout this series (sorry Serena and Dan), and if you don’t openly weep at Meester’s Blair saying her vows in that crisp ice blue Elie Saab gown, you’re a monster.

Plus, we get a flash forward to glimpse our favourite character’s lives down the road, and it’s pretty satisfying.

That’s it for now, UES. Now, we wait for the upcoming reboot.

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