In the 20 years since Gilmore Girls first premiered, a fierce debate has dominated much of the show’s discourse — one that, ironically, has little to do with Rory (Alexis Bledel) or Lorelai (Lauren Graham) Gilmore, the mother-daughter team at the centre of the series. Which of Rory’s three main boyfriends over the course of Gilmore Girls’ seven seasons — Dean, Jess, or Logan — was the best?
It’s almost a personality test at this point — each of the three loves of Rory’s early life are so different that they have come to represent different archetypes of the different kinds of guys that women tend to date. Revealing which one you prefer tends to say more about you than it necessarily does about the youngest Gilmore.
“Dean is for the settlers of the world,” says 28-year-old screenwriter Kate, who obsessively watched Gilmore Girls in high school. Dean (Jared Padalecki) was Rory’s first love, and the two had three relationships over the course of the show. Loyal and protective, he is a dependable boyfriend with boyish good looks who isn’t book smart like Rory but cares for her deeply. Dean is the kind of guy who won’t recite poetry to you, but he will change the bottle in your water cooler. Unfortunately, he lets his insecurity and jealousy get the best of him as Rory becomes closer to Jess (Milo Ventimiglia). Dean later cheats on his wife with Rory, which eventually leads to the dissolution of his marriage.
“I loved Dean always, and he treated Rory SO well because he loved her for who she is,” says Georgia native Olivia, 28, who watched the show when it first aired in 2000 and has continued to re-watch it ever since. “But he was a bit clingy towards the end, and the whole cheating on his wife thing is totally not okay.”
“Jess is for people who get off on a codependent relationship,” Kate says. Jess (Milo Ventimiglia), diner-owner Luke Danes’ (Scott Patterson) nephew, is the dark, messy hottie who breezes into town and sets his sights on Rory. He loves to read and can match Rory’s quick wit. Though Rory finally finds an intellectual equal, and Jess is the one who gets her back on track when she drops out of Yale, he’s also rash, unreliable, and appears to have an at-best muddled understanding of consent. Classic emotionally stunted bad boy behaviour.
“I hated him at first, but he was the only boyfriend who truly challenged Rory,” Olivia says. “They were alike in intellect and he was protective, which is cute… but also way too moody.”
And finally, there’s Logan (Matt Czuchry), Rory’s handsome college boyfriend who comes from a wealthy family that is close with Rory’s uppity grandparents. He’s a privileged playboy who gets Rory to finally loosen up in college — maybe even too much, given that he doesn’t stop her from dropping out of Yale the minute she’s dealt a blow to her self-esteem. He’s smart and loves Rory, but ultimately is content with skating along in life. Logan is used to things being handed to him on a silver platter, and his pretension drives a wedge between them. “Logan is a bit immature, he never viewed Rory as his equal, made her feel inferior, and changed her for the worse,” Olivia says.
“Logan is for folx who heart fuckbois,” Kate adds. “IMHO they never gave Rory anyone right for her. Maybe her best option was naked guy [Marty] until he got all incel-y on her.”
The debate has basically eclipsed all other conversations surrounding the show. The official Twitter TV account celebrated the pilot’s anniversary by sharing pictures of Dean, Jess, and Logan alongside the caption “It’s been 20 years. Make a choice.” Even TIME boasts a “definitive ranking of Rory’s hapless boyfriends.”
This isn’t what show creator Amy Sherman-Palladino likely imagined when she created Gilmore Girls, a show centred around female relationships — namely, that of Lorelai and Rory, but also Lorelai and her mother Emily (Kelly Bishop); Rory and her best friend Lane (Keiko Agena); Rory and best-frenemy Paris (Liza Weil); Lorelai and her eccentric best friend Sookie (Melissa McCarthy).
One could make the argument that the fans are responsible for this shift in the show’s focus. While Gilmore Girls was, in many ways, ahead of its time, so was Sex And The City — and fans still continue to fixate the Mr. Big versus Aiden versus Steve debate. We are still conditioned to view women through the lens of who they’re dating.
The 2016 revival, however, amplified the problem by framing nearly all of Rory’s narrative arc around her former flames. “While it’s true Rory is more than just her love life, when past and current romantic exploits are given centre stage like they were in the revival, you can hardly fault fans for placing so much emphasis on her complicated relationships,” wrote TV Guide.
It hasn’t helped that the general feeling towards Rory as a character has seemed to palpably sour. People felt like the struggling journalist was “immature” and blind to her own privilege. In a particularly scathing Rory takedown from The Washington Post, author Jenny Rogers wrote, “The new Gilmore Girls episodes only highlight the worst of Rory’s qualities: her impulsiveness, her selfishness, her inflated sense of her own worth, her tendency to quit at the first sign of trouble — and now she’s a grown woman, one who doesn’t seem to have learned from any of her mistakes. The revival also introduces us to a terrible new quality in her: amorality.”
Here’s another theory: The three men in Rory’s life were what she needed to find herself in the end and eventually come into her own (whether we like the end result or not). According to relationship therapist Dr. Danielle Forshee, PsyD, LCSW, Dean, Jess, and Logan could represent the different archetypes of personality that Rory had to meet along the way in order to achieve self-actualisation and unlock her full potential. “You see fulfilment through personal growth. When you find your authentic self, we are doing what we’re capable of, and we are fulfilled,” says Dr. Forshee. But therein lies the same conclusion: The show illustrated Rory’s coming-of-age through the various men she dated, rather than her growing on her own. This could help explain why it feels much easier for fans to talk about Rory as a character by way of talking about the three men who orbited her, since she ended up playing such a passive role in her own life.
Despite indulging fans’ obsessions with the Gilmore guys, Sherman-Palladino, however, makes a point at the very end of the show to circle back to the relationship that matters most. In the final scene of the revival, we see Rory as a single woman (spoiler alert: single future mom) relying on the support of her fierce, loving mother.
But anyways, Team Jess.
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