Despite the time that's ed by since the show's ending, Gilmore Girls remains a compelling viewing experience. However, re-watching the first season after two decades has revealed some quite upsetting truths about the show. Gilmore Girls debuted 24 years ago, and stole the hearts of its viewers with its quick-witted dialogue and heartwarmingly relatable character dynamics.

However, not every aspect of Gilmore Girls has stood the test of time. Society has progressed rapidly since the year 2000, and so has the show itself. The twists and turns of Gilmore Girls’ concluded storyline, along with a drastically changed societal perspective, means that season 1 of the comedy-drama sometimes breaks the viewer out of an autumnal daydream, and instead brings a harsh reality.

10 So Much Fatphobia

A Look at Unhealthy Body Image Portrayals

Throughout season 1 of Gilmore Girls, the topic of weight-gain and an emphasis on food-guilt reoccurs an unhealthy amount. From Lorelai’s casual jokes that condemn being “fat and happy” in the second episode, to sprinkled food-shame throughout the season, Gilmore Girls isn’t perfectly inclusive.

Unfortunately, it makes sense that a show so synonymous with the 2000s would include elements of fatphobia, but it doesn’t make the jokes any less gutting. Re-watching in 2024, after living through the much-needed body positivity movement, means that these jabs leave a sour taste in the mouth. It’s important to note that Sookie, a plus-sized character, is handled incredibly well in her writing, and focuses more on her skill than size. But having two thin protagonists often make food-shaming comments while simultaneously living off junk food and coffee sets incredibly unrealistic standards for young Gilmore Girls viewers.

9 Dean Was A Major Red Flag

Exploring the Toxic Dynamics of Their Relationship

Rory’s young suitor might not be as romantic as he initially seemed. Dean telling Rory that he’s been “watching” her in the pilot should have made her cautious of him, let alone his overly jealous and possessive nature when he jumps the gun after seeing Rory interact with Tristan at her school dance.

Like when he pressures Rory to say “I love you” despite her not being ready. It’s no surprise that Dean turns out the way he does in the later seasons.

Especially on a re-watch, knowing where Rory’s love story with Dean ends in Gilmore Girls, it’s kind of impressive that these red flags didn’t jump up on the first watch. Dean shows all the signs of an immature and toxic boyfriend, like when he pressures Rory to say “I love you” despite her not being ready. It’s no surprise that Dean turns out the way he does in the later seasons, as his caring demeanor was clearly a bad disguise for serious boundary issues - it showed from the very start.

8 Lorelai Wasn’t A Great Parent

Examining the Flaws in Her Mothering

While their dysfunctional dynamic was truly the heart of the show, Lorelai’s parenting style in Gilmore Girls wasn’t always the healthiest. Lorelai sometimes comes across as temperamental, for example, treating Rory like a friend the entire season only to whiplash into a furious parent when Rory gets home late in episode 9.

It does make complete sense, as Lorelai had Rory so young it’s only natural that her parental dynamic with Rory would seem more like that of siblings, but this fun, light-hearted approach to parenting can have serious consequences. Although Rory is famously a “good kid,” any teenage girl needs to have a strong parental influence, and Lorelai wasn’t always able to provide that for Rory. While Gilmore Girls would fall flat if not for its realistic character flaws and unconventional mother-daughter dynamics, it’s important that Lorelai’s parenting style isn’t overly romanticized.

7 Lorelai Wasn’t Really A “Self-Made” Mom

Debunking the Myth of Her Independence

While Lorelai has every right to be proud of the life she made for herself after leaving home, she’s far from being a self-made mother. Lorelai is lucky to have raised such a gifted child, but Rory would never have been able to pursue her potential if it weren’t for her grandparents, Emily and Richard, being able to pay the Chilton tuition.

Even though Lorelai swore off her parents’ help, there’s a level of comfort to her character that wouldn’t be there if Lorelai didn’t come from a privileged background.

Lorelai may be self-sufficient because of her job at the hotel, but most mothers in her position would not have been able to encourage their child to apply to a private school, or would have had to take up other jobs in order to do so. While Lorelai may not have lived off her parents’ money, she certainly lived with the comfort of knowing it was there for her.

6 Tristan’s Persistence Went Too Far

Analyzing the Line Between iration and Harassment

On the initial watch, Tristan’s cocky bad-boy determined attitude surely made some viewers swoon, but on the re-watch, Tristan’s persistence was kind of unnerving. Tristan was played by Chad Micheal Murray, a renowned heartthrob of the 2000s, so it makes sense that his character’s flaws were originally ignorable, but his unrelenting approach just s as creepy today.

Tristan was clearly being set up as a love interest for Rory before his actor left in the following seasons, but without a redemption arc, his constant teasing and unwanted advances make the character irritating to watch. His behavior is framed as typical teenage flirting, but Rory’s consistent rejection and discomfort after he attempts to win her over make Tristan seem like an entitled rich boy who can’t take no for an answer.

5 Christopher’s Return Wasn’t Fair

Evaluating the Impact of His Re-entry into Lorelai’s Life

Christopher’s return to Stars Hollow in episode 15 was not fair to Rory. After being absent for most of Rory’s upbringing, Christopher returns and expects Lorelai to fall for him again by promising a stable life that he didn’t actually have.

Not only is that unfair on Lorelai, who is being made to feel like she’s pushing her child’s father out of her child’s life, but it’s incredibly inconsiderate to Rory, who is perceptive enough to understand her father’s intentions. Christopher doesn’t take ability for his actions or absence, and even complicates things further for Rory, like when he asks her to lie for him after his card declines. Lorelai’s lingering feelings and Rory’s iration of her father seem to pardon Christopher for his incredibly problematic behavior, and the character should’ve faced more consequences for his actions.

4 There’s Nothing Wrong With Being A Homemaker

Challenging Stereotypes About Domesticity

In episode 14, Lorelai and Rory mock the concept of a traditional homemaker after watching The Donna Reed Show. Rory does attempt to embrace the idea for Dean, but the show treats it as a joke.

The treatment of the homemaker archetype is problematic for several reasons. Gilmore Girls is incredibly dismissive of those who opt to be a homemaker and enjoy traditional gender roles. It goes against the purpose of feminism, which is a woman's right to choose how to spend her life. Additionally, when the idea of a homemaker is explored further within the show, it is not only done in a comedic manner but only done because Rory wants to please Dean, which further alienates the homemaker archetype as being a respectable life decision that a woman is allowed to make.

3 Lane’s Dreams Were All For Nothing

Discussing the Disappointment of Unfulfilled Aspirations

It’s almost heartbreaking to re-watch the series 24 years later after seeing how Lane’s storyline concluded in Gilmore Girls. Throughout the entirety of season 1, the audience is introduced to Lane as a sheltered teen who is desperate for freedom and independence.

So it’s hard to watch her younger and more hopeful self on screen without an impending sense of dread.

Watching Lane navigate the world with wonder and ambition while knowing what happens in later seasons, makes every scene with her rambunctious attempts at independence seem largely depressing. In the later seasons, Lane settles into married life with a lackluster honeymoon and an immediate unplanned pregnancy, neither of which is portrayed as incredibly fulfilling to Lane, who had dreams of whirlwind romances and world tour concerts. So it’s hard to watch her younger and more hopeful self on screen without an impending sense of dread.

2 Rory Really Should’ve Addressed Her Academic Anxiety

Exploring the Consequences of Ignoring Mental Health

When re-watching episode 4, where Rory breaks down after getting a bad grade at Chilton, there’s an incredibly clear issue within Rory’s storyline. She absolutely should’ve addressed her academic anxiety.

Rory values her intelligence above everything else in the show, and has strict dreams and a stricter plan regarding her academic career. However, with her high standards taking a toll on her mental health so early in the show, it’s apparent that Rory should’ve addressed the immense pressure placed upon her to succeed. Especially when the same pressure leads to Rory impulsively dropping out of Yale in the later seasons of the show. If Lorelai or anyone around Rory had noticed her anxiety, rather than deeming it a quirk, she likely would’ve had a much easier time in her later seasons.

1 Emily Did Not Go First

Examining the Mother-Daughter Dynamic and the Importance of Prioritizing Needs

In an emotional moment in episode 10, after Richard ends up in the hospital, Emily struggles with her denial of his condition before eventually asserting that he has no choice but to be fine, because she has decided she will “go first.” It was a tear-jerking moment on the first watch and manages to still leave a similar impression after nearly two decades, because of the painful awareness that Richard does, in fact, "go first." In a show so central to love and life, it’s natural that the harshest reality will be in the presence of death, and the show does an amazing job of writing about it. Despite its many flaws, Gilmore Girls’ harshest realities could never undermine what a beautifully layered story each character created.