There's no denying that Gilmore Girls is a beloved classic, a show that defined a generation with its rapid-fire dialogue, quirky small-town charm, and the unbreakable bond between Lorelai and Rory Gilmore. For many, it's the ultimate comfort watch, a cozy escape into the world of coffee, bookworms, and town meetings. But as with any show from the early 2000s, a rewatch through a modern lens reveals some cringe-worthy moments that haven't aged gracefully.
From questionable jokes about body image to storylines that romanticize toxic behavior, several episodes of this otherwise progressive series now feel dated. While the show's popularity hasn't waned—thanks in part to its streaming success—it's worth examining the episodes that spark the most discomfort today. Here's a look at some Gilmore Girls episodes that don't quite hold up, from the original run to the 2016 revival.
“A-Tisket, A-Tasket” (Season 2, Episode 13)
The annual Stars Hollow charity basket auction is a fan-favorite tradition, but this episode is problematic for its portrayal of jealousy and possessiveness. When Jess wins Rory's basket, Dean's reaction is unsettlingly aggressive. Instead of addressing the issue healthily, the show frames his anger as a natural response, setting a troubling precedent for his character's behavior later on. It's a classic example of normalizing toxic masculinity in teen dramas.
“Here Comes the Son” (Season 3, Episode 21)
This episode is less about offensive content and more about a narrative misstep. It was clearly designed as a backdoor pilot for a Jess spin-off, which never materialized. As a result, the focus shifts awkwardly away from Rory's graduation and Lorelai's financial struggles to Jess's journey to California. The tonal shift feels jarring and disrupts the show's otherwise cohesive storytelling, making it a standout for all the wrong reasons.
“Girls In Bikinis, Boys Doin' The Twist” (Season 4, Episode 17)
Rory and Paris head to Florida for spring break in this episode, which is a mixed bag. On one hand, it's hilarious to see these bookish girls out of their element. On the other, the episode is steeped in early-2000s clichés and a “not like other girls” attitude. Rory and Paris constantly judge the other spring breakers, reinforcing a tired trope that intellectual women are superior to those who enjoy stereotypical vacation activities. It's a dated perspective that doesn't sit well today.
“That's What You Get, Folks, For Makin' Whoopee” (Season 7, Episode 2)
This episode is a prime example of cultural insensitivity. After Lorelai sleeps with Christopher, she tries to cheer up Rory by creating an “Asian wonderland” at home, complete with stereotypical decorations. It's a cringe-worthy attempt at cultural appreciation that comes off as offensive and ignorant. Combined with the season's overall controversial storylines, this episode is a low point for the series.
These episodes are a reminder that even our favorite shows are products of their time. While Gilmore Girls remains a beloved series, it's important to acknowledge its flaws. For a more positive look at the show, check out our list of the most flawless episodes. And if you're in the mood for more TV critiques, we've also ranked the most unsettling TV episodes of all time.
