The Ultimate Ranking: Every Gossip Girl Thanksgiving Episode, From Iconic Drama To Reboot Disasters

The annual Gossip Girl Thanksgiving episode is less about turkey and gratitude and more about explosive family secrets, shocking betrayals, and the most dramatic confrontations the Upper East Side has to offer. For fans revisiting the series in late 2025, these holiday specials remain the gold standard for peak teen drama, consistently delivering the series’ most pivotal plot twists right over the Van der Woodsen-Bass-Humphrey dinner table. From the original series' five iconic holiday installments to the HBO Max reboot's attempt, these episodes prove that nothing spices up the holidays quite like a perfectly timed secret being revealed.

The core appeal of these holiday episodes lies in the forced proximity of the main characters—Blair Waldorf, Serena van der Woodsen, Chuck Bass, Nate Archibald, and Dan Humphrey—as their tightly controlled worlds inevitably collide during a supposed day of peace. The recurring theme is the unraveling of a major secret, often involving Lily van der Woodsen or Rufus Humphrey, that sends seismic shockwaves through the entire group, cementing Gossip Girl's legacy as a masterclass in holiday-themed chaos.

The Complete List of Gossip Girl Thanksgiving Episodes & Their Explosive Plot Points

The original series (2007-2012) delivered five memorable Thanksgiving episodes across its six seasons, each one escalating the drama from the last. The reboot (2021) also attempted to carry on the tradition. Here is a comprehensive look at every episode that turned the holiday into a battlefield.

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• Season 1, Episode 9: "Blair Waldorf Must Pie!" (Original Air Date: November 28, 2007)
  • The Drama: This episode sets the tone, featuring flashbacks to a pre-Upper East Side friendship between Dan and Serena. The main event, however, is the revelation of Blair's struggle with bulimia, triggered by her father's affair and subsequent absence, adding a layer of depth to her character.
  • Iconic Moment: The tense, emotional confrontation between Blair and her mother, Eleanor Waldorf.
• Season 2, Episode 11: "It's a Wonderful Lie" (Original Air Date: December 1, 2008)
  • The Drama: While not strictly a Thanksgiving episode (it's a Christmas/New Year's hybrid), the Season 2 mid-season break often features holiday drama. However, the true Thanksgiving episode for Season 2 is often cited as a general holiday-themed installment that focuses on relationship fallout, primarily between Chuck and Blair, following the events of the previous episodes.
• Season 3, Episode 11: "The Treasure of Serena Madre" (Original Air Date: December 7, 2009)
  • The Drama: The undisputed champion of Gossip Girl drama. The entire episode is a slow-burn disaster culminating in the revelation that Lily van der Woodsen sold her mother's apartment to pay for a secret medical procedure for her ex-husband, William van der Woodsen. The episode also features Vanessa Abrams revealing a major secret about Serena's past.
  • Iconic Moment: A tense, silent dinner where everyone knows everyone else's secret, culminating in Lily's confession. This episode is widely considered the best of the holiday specials.
• Season 4, Episode 10: "Gaslit" (Original Air Date: December 6, 2010)
  • The Drama: This installment is arguably Gossip Girl at its most convoluted and dark. Juliet Sharp drugs Serena, leading to her hospitalization and a tense Thanksgiving dinner where the group attempts to uncover the truth behind Serena's erratic behavior, with Blair and Chuck on the outs.
  • Iconic Moment: The group uniting to expose Juliet, showing a rare moment of solidarity among the core five.
• Season 6, Episode 8: "It's Really Complicated" (Original Air Date: December 3, 2012)
  • The Drama: The final Thanksgiving episode of the original series. Dan is working on his explosive exposé, which causes Nate Archibald to punch him square in the face—one of the episode's highlights. The episode focuses heavily on Dan and Serena's complicated relationship and the drama surrounding the reveal of Dan's book.
  • Iconic Moment: Nate punching Dan, a moment of cathartic release for fans who felt Dan had crossed a line.
• Reboot Season 1, Episode 7: "Once Upon a Time in the Upper East Side" (Original Air Date: December 2, 2021)
  • The Drama: The reboot's attempt focuses on a complicated love triangle involving Julien, Obie, and Zoya, alongside a betrayal-filled triangle between Audrey, Aki, and Max. The episode was generally well-received by fans of the new series, with some calling it the best installment of the season.
  • Iconic Moment: The dramatic tension between the new generation of Upper East Siders as their secrets are exposed via the new, teacher-run Gossip Girl account.

Why "The Treasure of Serena Madre" Remains the Undisputed Champion

When fans and critics rank the Gossip Girl Thanksgiving episodes, Season 3, Episode 11, "The Treasure of Serena Madre," consistently takes the top spot. This episode is a masterful example of the show's formula: confining all the characters to the Van der Woodsen penthouse for an elegant dinner, only to have their biggest secrets explode like a hand grenade. The episode’s success is rooted in its perfect balance of high-stakes family drama and romantic turmoil.

The central conflict revolves around Lily and Rufus, whose seemingly stable relationship is rocked by the revelation of Lily's past actions. Rufus, trying to maintain a sense of normalcy, is completely blindsided. Simultaneously, the love triangles are at their peak: Serena is hiding secrets about her father, Dan is wrestling with his feelings, and the tension between Blair and Chuck is palpable, even if they aren't the main focus. The episode’s title, a reference to a complex plot involving Lily's mother, CeCe Rhodes, and the sale of an apartment, underscores the deep-seated, generational secrets that plague the Upper East Side elite. This density of secrets, all exposed in a single, tense dinner scene, is what makes it a classic. It’s a showcase of dramatic irony, where the audience knows the secrets, watching the characters squirm before the inevitable reveal.

The Enduring Legacy of Holiday Drama and Iconic Fashion

Beyond the plot twists, the Gossip Girl Thanksgiving episodes are essential viewing for their aesthetic and cultural impact. The holiday setting allows the show's costume designer, Eric Daman, to showcase some of the most memorable and stylish holiday outfits. Blair Waldorf, in particular, always delivered impeccable holiday fashion, often wearing rich jewel tones and classic silhouettes that contrasted sharply with the messy reality of her life. The juxtaposition of elegant, picture-perfect settings—like the lavish Van der Woodsen dining room—with the utterly chaotic and toxic emotional landscape is a core element of the show's genius.

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The episodes also provide crucial character development. "Blair Waldorf Must Pie!" (S1, E9) was vital in humanizing Blair, moving her beyond the 'Queen B' caricature to reveal her vulnerabilities and the deep-seated trauma caused by her family's instability. This episode provided a necessary foundation for her later relationship with Chuck Bass, which often revolved around their shared family issues and emotional baggage.

While the 2021 reboot's Thanksgiving episode, "Once Upon a Time in the Upper East Side," was a high point for the new series, it struggled to capture the same level of iconic, high-stakes family drama as the original. The original series benefited from the deep history and complex relationships built over multiple seasons, making the holiday reveals feel more earned and devastating. The reboot, with its focus on love triangles and a more modern, less centralized drama, felt like a sad emulation in comparison to the sheer power of the original's holiday classics.

Key Entities and LSI Keywords Driving the Topical Authority

To fully appreciate the depth of the Gossip Girl Thanksgiving canon, one must recognize the recurring entities and themes that define them:

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• Blair Waldorf: Her emotional arc, family secrets, and iconic fashion are central to the holiday episodes.
• Serena van der Woodsen: Her complicated past and her relationship with her father, William van der Woodsen, often drive the major holiday plot lines.
• Chuck Bass & Nate Archibald: Their roles often involve supporting the women or engaging in their own high-stakes business and romantic scandals.
• Dan Humphrey: The 'Lonely Boy' and his journalistic ambitions, culminating in his explosive exposé, were a major source of conflict in the final season's Thanksgiving dinner.
• Lily van der Woodsen & Rufus Humphrey: The "adult" drama, particularly Lily's secrets and Rufus's disillusionment, is the foundational layer of chaos.
• Vanessa Abrams: Her brief but impactful role in revealing a major secret in Season 3 is a key plot point.
• Topical Keywords: Upper East Side, Family secrets, Love triangles, Iconic fashion, Dramatic moments, Thanksgiving dinner, Plot twists, and Betrayal.

Ultimately, the Gossip Girl Thanksgiving episodes are a perfect time capsule of early 2010s television drama, blending high fashion, generational wealth, and deeply personal secrets. As fans continue to revisit these moments in 2025, the tradition of watching the Van der Woodsens and Waldorfs implode over a perfectly carved turkey remains an essential part of the holiday season.