#98 TRENDING IN Opinion πŸ”₯

Spilling the Tea: Ranking of Every Iconic Gossip Girl Episode


June 30, 2023

Hello, my fellow gossipers! I'm sure all of you have grown up to have either heard about or watched gossip girl at some point. 11 years later and the show is still as memorable as ever. From TikTok clips to Twitter memes, Gossip Girl's popularity definitely has not and probably will never die out anytime soon. As a fellow New Yorker, I feel like it is my duty to give the readers a ranking of ten of the most iconic episodes of Gossip Girl to date.

View this post on Instagram

A post shared by Gossip Girl (@gossipgirlfeed)

10. "The Pilot" Season 1, Episode 1

Every good story usually has humble beginnings, but Gossip Girl is a prime example that sometimes it's better not to follow the norm. The story kicks off with audacious flair, unveiling a world brimming with scandal and secrets amongst New York's elite. From the very first scene, the lavish lifestyles of Serena van der Woodsen, Blair Waldorf, Nate Archibald, Chuck Bass, and Dan Humphrey unfold before our eyes.

It's also where we get to see Serena's memorable photo taken by a random bystander who tries to rat her out to gossip girl that she's back in town, sending shockwaves through the tightly knit social circle. The cinematography of the pilot episode is nothing short of breathtaking (at least for 2007). The opulent locations, from the majestic corridors of Constance Billard School for Girls to the extravagant penthouses overlooking the glittering cityscape, capture the glamor and sophistication that define the Upper East Side. One of the most interesting aspects of the episode is the introduction of Gossip Girl herself—a mysterious and all-knowing blogger who holds the power to expose the secrets of the Upper East Side's elite and basically ruin their entire social lives. Overall, this episode is perfect for the audience to get a better handle on the Gossip Girl universe while bringing viewers back for more. It's why this episode has earned the #10 spot on the list.

View this post on Instagram

A post shared by Gossip Girl (@gossipgirll)

9. "The Townie" Season 4, Episode 11

This episode focuses on Juliet Sharp's manipulations and schemes, leading to the exposure of her true intentions. The tension and drama escalate as her schemes impact Serena, her friends, and her loved ones. The ripple effects of her manipulations create a sense of uncertainty and keep viewers on the edge of their seats, eagerly anticipating the fallout.

It was revealed that her brother Ben taught at Knightly, the Connecticut boarding school S attended after leaving Manhattan prior to season 1. He and Serena became closer until she caught feelings for him—even making advances towards him when they found themselves stranded in upstate New York after taking a trip to Vassar. Despite rejecting Serena, the school was informed that Ben had slept with a student, even obtaining an affidavit confirming the allegations. Ben was told that if he accepted a plea bargain, he could serve a five-year sentence for statutory rape and transporting a minor across state lines. Hence, why he's in jail and is convinced that Serena ruined his life. The truth comes throughout the episode as Dan and Blair head to Connecticut with the goal of finding Juliet. After getting a tip from Gossip Girl herself, Dan and Blair continue their search until running into Damien Dalgaard, the preppy drug dealer who went to Knightly with Serena. He lets them know that he sold Juliet the pills she used on Serena. Juliet discovers D and B are onto her and heads straight to Serena only to reveal her plans. But when she explains that her actions were because of Ben, Serena is confused because she never signed the affidavit until she realizes who forged her name. Surprise! It's Lily! After a heated discussion between the mother-daughter duo, Serena states that she will never "have to do anything for [Lily]" ever again. This episode has earned the #9 spot as the audience is taken on a suspenseful journey as Juliet's web of lies begins to unravel, and her true colors are revealed. It's a testament to the show's ability to create complex and multifaceted antagonists, adding layers of intrigue to the overall narrative.

8. "The Freshmen" Season 3, Episode 2

Despite Blair being desperate to continue her Queen B status at NYU, she runs into a familiar yet unwelcome face: Georgina Sparks. She has arrived at NYU, and like a mischievous enchantress, she's woven a spellbinding web across the city. Georgina is so popular that she even becomes buddy-buddy with Vanessa, who gives G a second chance despite her very shady past.

In typical Blair fashion, she decides there is only one way to win over a crowd of people: a sushi soirée. However, nobody else was interested in the party, which led to Georgina calling Blair an outcast. So what does one do in desperation? The unthinkable. Blair asks Dan to be his date to Georgina's party, and she seems content trying to assimilate with her classmates, but in typical Blair fashion, she's up to something huge. She got people from Georgina's Christian camp to crash the party, then hijacked the mic to out Georgina for being a Jesus freak. Dan comes to Georgina's rescue by exposing Blair's plans and convincing the crowd to get drunk with him. Blair stalks back to Chuck and spends the rest of the evening with him despite her failed plans. While this episode may not have been as drama-filled as the other episodes, I do think that it earns a spot on the list because it properly introduces the characters into college and sets the stage for future developments in a different setting. Plus, who doesn't like a mini showdown between Blair Waldorf and Georgina Spark?

View this post on Instagram

A post shared by Blair Waldorf (@blairwaldorfbass)

7. "G.G." Season 5, Episode 13

We already knew that episode 100 was bound to be a good one, and what's better than a royal wedding? Blair makes a life-changing decision to marry Prince Louis after reeling from the end of her and Chuck. This marriage turns out to be for looks once Louis reveals to Blair that their marriage is a contract.

Blair calls out to Dan for help, and he comes in to help, mostly due to his strong feelings for her. With Georgina taking the reins on the Gossip Girl account, disaster is bound to strike. All Blair wanted was to be a Princess, yet she couldn't get Chuck out of her mind. No matter how many ups and downs they go through, their love is so strong that not even a prince can come between them (#Chair). As the identity of Gossip Girl is finally unmasked, this episode delivers on the show's promise of scandal, intrigue, and deliciously wicked entertainment.

6. "Pret-A-Poor J" Season 2, Episode 8

I love how the episode grabs the audience's attention with its fast-paced storytelling and visually stunning pieces. The fashion element takes center stage as Jenny Humphrey finds herself caught between her desire to fit into the glamorous world of the Upper East Side elite and her determination to maintain her own identity. She's an intern for Eleanor Waldorf, and she befriends a model beamed Agnes.

Unknowingly, Agnes helped her realize that Eleanor was taking advantage of her designs. So, she decides to quit working for Eleanor and start her own designs. After getting into a bit of trouble with Agnes, Nate comes to the rescue and starts to see Jenny for more than being Dan's little sister. One of the main things I like is how we explore the power dynamics between Jenny and the Waldorf family, especially Eleanor, and Blair. It's also interesting to see Jenny go "dark" as she finally realizes her worth and makes a 180 change of the century (apart from Georgina, of course).

View this post on Instagram

A post shared by Gossip Girl (@gossipgirl)

5. "Last Tango, Then Paris" Season 3, Episode 22

The tension is palpable, with Blair and Chuck's complicated relationship reaching a crucial turning point. In a whirlwind of events, a seemingly innocent sleepover between Serena and Dan becomes the catalyst for a chain of life-altering moments in this gripping episode. With just a kiss shared between the former lovers, the repercussions ripple through everyone's lives.

Little J, ever the schemer, captures a compromising photo of Serena and Dan, unleashing chaos when it's spread by Gossip Girl. The fallout is inevitable. As Nate finds himself upset, Dan questions his relationship with Vanessa and reevaluates his feelings for Serena. Jenny's actions spiral out of control, leading Rufus to send her away to Hudson. Meanwhile, at the hospital, a shocking revelation about Chuck and Jenny's involvement drives a furious Dan to confront Chuck, resulting in a devastating confession. The consequences prove too much for Blair, who decides it's over between them. Blair and Serena embark on a new journey to Paris while Jenny heads off to Hudson. Chuck's life takes a dangerous turn when he is shot in Prague, losing the engagement ring meant for Blair. I enjoyed how this episode masterfully balances heart-wrenching moments with unexpected twists, keeping the audience hooked until the very end.

View this post on Instagram

A post shared by Gossip Girl (@gossipgirl)

4. "The Revengers" Season 6, Episode 9

Everything kicks off with a dream sequence where Blair and Chuck play a game with an orange, setting the tone for the intrigue and tension to come. Meanwhile, Dan is apartment hunting with Georgina, only to discover that he needs a good reference to secure the perfect place. Chuck and Blair hatch a plan to expose Bart's crimes at a party, with Ivy playing a crucial role.

However, Bart arrests and uses Nate as bait, leaving the group shocked and desperate for a solution. While Serena tries to make amends with Ivy, Dan strikes a deal with Bart to write a favorable article in exchange for a recommendation. Chuck and Serena confront Bart separately, leading to a dramatic confrontation that results in Chuck making a difficult decision. The episode ends with Blair orchestrating a plan to take down Bart, Dan revealing his true feelings to Serena, and a shocking twist that leaves Bart's fate uncertain. This episode raised so many questions for me as the season finale was approaching. Is Dan bad? Will Chuck and Blair get their happily ever after? Who is the real Gossip Girl? For the 2nd to last episode, I found that this episode was so full of suspense, especially when Bart Bass is (hopefully) presumed dead after suffering a tough fall off a 100-story skyscraper. Overall. It was a great build-up to the ending that will close out this story.

View this post on Instagram

A post shared by gossip girl fans!! (@xoxogossipgirlfanss)

3. "The Treasure of Serena Madre" Season 3, Episode 11

Thanksgiving plans and secrets unfold among the characters. Rufus reluctantly agrees to Lily's plan of buying a ready-made dinner instead of cooking. Eric suggests inviting CeCe over video chat, but Jenny secretly invites Jonathan despite their recent breakup.

Meanwhile, Serena confronts Tripp about his impending divorce, leading to their plans for Thanksgiving being canceled. At the Waldorf's, Blair suspects Eleanor is keeping a secret and later discovers a pregnancy test, only to find out it belongs to Dorota. Nate tries to expose Tripp's affair with Serena, while Chuck advises him to tell Serena his true feelings. Lily and Rufus host a Thanksgiving dinner where various tensions arise, including the revelation of CeCe's remission and a tape that exposes Serena and Tripp's affair. Serena decides to leave with Tripp, Nate confesses his feelings to her, and a letter from Serena's father reveals new information. The episode ends with significant developments, including Vanessa and Gabriella moving to a hotel, Dorota revealing her pregnancy to Vanya, and the mystery surrounding the letter addressed to Serena's father. Obviously, I had to put this episode up there simply because of the iconic dinner table scene in Jason Derulo's Whatcha Say. I feel this episode takes the cake out of all the Thanksgiving specials. From Blair's usual sassy dialogue banning thanksgiving in her life (for 10 minutes) to Dorota's ringtone that funnily represents her job, I feel like the writing in this episode is sharp and clever, with witty dialogue and well-crafted plot twists. The pacing keeps the story moving forward, ensuring there is never a dull moment.

View this post on Instagram

A post shared by Gossip Girl (@gossipgirl)

2. "The Goodbye Gossip Girl" Season 2, Episode 25

Blair and Serena share breakfast before their graduation. They discuss Serena's recent arrest and the increased publicity surrounding her. Serena hopes for a break from Gossip Girl after graduation, as the platform doesn't report on college.

Chuck confesses his love for Blair, but Blair realizes he doesn't know about her breakup with Nate. At Constance/St. Jude's Nate interacts with William and Vanessa, revealing his internship plans and the breakup with Blair. Meanwhile, Jenny encounters the girls holding a contest to determine the next queen of Constance, and Blair decides to reclaim her authority. A Gossip Girl blast labels the main characters with derogatory titles during graduation, leading Serena and her friends to plot against Gossip Girl. Eventually, they discover Jonathan as the person behind the Gossip Girl persona. At Nate's graduation party, tensions rise among the group as secrets are exposed, causing rifts between them. Ultimately, Serena and Blair reconcile, and they uncover the truth behind Gossip Girl's identity. In the end, Blair reunites with Chuck, Serena prepares for a trip to Europe, and other characters begin new chapters in their lives. If this episode has proved anything, it's that gossip girl is not someone you want to mess with. Seeing the power move that gossip girl pulls to keep everyone in line was interesting. It kept me on my seat and made me wanna see what other chaotic actions G.G. could pull. I also like how this episode closes out the high school chapter and opens the characters to new experiences and a new set of challenges.

1. "New York, I Love You XOXO" Season 6, Episode 10

Just like every story has a humble beginning, stories also must come to an extravagant end. The aftermath of Bart's death unfolds in the series's final episode. Blair and Chuck escape the scene while Georgina overhears about the body and informs Blair for help.

They hide in a bed and breakfast, where Jack finds them and reveals Bart's death. Serena discovers the final chapter of Dan's book, realizing his role in creating Gossip Girl. Blair and Chuck decide to marry, seeking spousal privilege. Lily returns and is comforted by William. Meanwhile, Nate discovers he can own The Spectator, but his concern is for Chuck's well-being. The group reunites at The Met, with Blair and Chuck planning a wedding at Bethesda Fountain. The police interrupt the ceremony, and it is revealed that Dan was Gossip Girl all along. The group processes the revelation, and five years later, Nate is considering a mayoral campaign. The scene shifts to a joyful gathering. It is implied that a new Gossip Girl has emerged, hinting that the cycle continues. Finally, Dan and Serena get married, and a new generation is introduced, suggesting the perpetual allure of the Upper East Side. After 6 seasons of ups and down, it makes sense for the episode to wrap up with Blair and Chuck's wedding, Bart finally being dead, and a time skip. It was enjoyable to see the back-and-forth between Blair and Chuck end with a mini-Chuck running around on the screen. Not sure if this is a popular opinion, but Serena and Dan should not have ended up together, and it should have been Nate instead. That aside, this episode is a fitting finale for Gossip Girl, delivering a rollercoaster of emotions, jaw-dropping revelations, and closure for our beloved characters.

View this post on Instagram

A post shared by πŸ‡«πŸ‡· Morgane ~ Nice, France. (@morganiglo)

Murders, Lies, Scandals, and Drama. Our favorite Upper East Siders have been through it all! While this ranking may reflect my personal opinion, I do think that these episodes were the most entertaining to watch.

Hopefully, this post has inspired you to rewatch Gossip Girl. Feel free to leave your preferred episodes in the comments, and let me know why they were your favorite! XOXO!

Williana Serve
100k+ pageviews

Williana is currently a freshman in college. She likes to learn new things especially involving Law & Advocacy. When she’s not doing schoolwork, she can be found watching TikTok, YouTube, or reading.