Gilmore Girls: Rory Gilmore’s relationships, ranked worst to best

As the beloved series turns 20 this year, Roisin O’Connor looks at the pivotal relationships of Rory Gilmore

Gilmore Girls celebrates its 20th anniversary this year

This year, 5 October will mark the 20th anniversary of the first ever episode of Gilmore Girls, a series that has gone on to enjoy cult status among its fans.

The show followed the lives of Lorelai Gilmore and her teenage daughter, Rory, in the quirky fictional town Star’s Hollow. While it was heavily focused on the mother-daughter relationship of Lorelai and Rory, it also dealt with their respective relationships, heartbreak, dreams and disasters.

To celebrate the anniversary (as well as actor Alexis Bledel’s birthday on 16 September), here’s a ranking of Rory Gilmore’s relationships, worst to best.

Paul 

What was the point of Paul? In 2016’s misjudged Gilmore Girls: A Year in the Life miniseries – the Netflix sequel to the original show – Rory is dating the hapless Paul (Jack Carpenter), whom she keeps forgetting exists, let alone that she’s in a long-term relationship with him. Rory is also cheating on Paul with her old flame, Logan. It’s not really Paul’s fault that he comes at the bottom of the list, but he was by far the worst written and most pointless relationship of the entire series.

Logan Huntzberger 

A lot of GG fans like to defend Logan (played by Matt Czuchry), Rory’s university boyfriend, but really, what are his redeeming qualities? He calls Rory weird pet names like “Ace” and “Pigeon”, like she’s a pet that he’s temporarily fond of. He claims to want to escape the pressures of his wealthy family’s legacy (his father is a powerful newspaper magnate) but still enjoys the perks that come with being ludicrously rich. He’s a playboy who is supposedly “tamed” by Rory, but who – when they go on a relationship break – promptly sleeps with an entire bridal party, then gaslights Rory into thinking it’s no big deal. When he fails at a work venture and ends up getting sued, he runs off to Las Vegas with his mates while his father’s company cleans up the mess. 

His and Rory’s relationship is also full of petty bickering and childish antics that lead to them both getting arrested after Rory persuades him to steal a boat. When Rory (sensibly) tells Logan she’s too young to get married but wants to be with him, he ends things, only to later start sleeping with her when he’s engaged to another woman. Basically, they were a terrible influence on each other – the epitome of a toxic relationship.

Dean Forrester

Lorelai once described Dean (played by Jared Padalecki) as the “perfect first boyfriend”, which was, in many cases, true. Dean was tall, handsome in a Hollywood Golden Age kind of way, and he loved Rory. Unfortunately, his behaviour was often less than desirable – Dean was jealous of any other boy who showed interest in Rory and this often (always) led to violence, or threats of violence. And while he never pressured her for sex when they were together, he cheats on his wife with Rory just a few months after getting married. 

There was also the issue that Rory and Dean had very little in common: Rory was ambitious and set on attending Harvard, while Dean was complacent if not downright against the idea of going to college.

Jess Mariano

Fans of Jess (Milo Ventimiglia) and Rory can cling on to the fact that it was implied, at the end of A Year in the Life, that their relationship might follow the same pattern as Lorelai and Luke (Jess’s uncle). He arrives in Rory’s life as a troubled, bitter teenager sent away from his home in New York by his mother, and quickly raises hell in sleepy Stars Hollow. Yet he proves to be Rory’s intellectual equal, someone who challenges her and shares her love of books and music. There will forever be a mark against him for an unnerving scene where he tries to have sex with Rory at a party when she clearly does not consent, then blows up at her when she calls him out for it. 

However, Jess is one of the few characters who really grew up. He drops his “the world’s against me” attitude, gets a job at a bookstore and writes a book. When he comes back into Rory’s life, he questions her decision to drop out of Yale and abandon her dreams of being a journalist – as well as her motives for being with Logan, the kind of guy they used to mock. This proves something of a wake-up call, and soon after she moves back out of her grandparents’ house, fixes her relationship with Lorelai, gets a job at a newspaper and returns to Yale. We see Jess inspiring her again when she finds herself back in Stars Hollow, a graduate with no job prospects and no idea of what to do with her life, when he suggests that she writes a book about the Gilmore Girls. Even Rory’s impossible-to-please best friend Paris approved of him. Speaking of…

Paris Geller

 Surprise! Of course, this isn’t a “romantic” relationship but, excluding the one with her mother, this is Rory’s most pivotal relationship in the entire show. Paris is the one constant in Rory’s life, there even when she’s not speaking with her mother. She’s equal, if not superior, to Rory’s intellectual abilities, and unstoppable when it comes to achieving her goals. Paris and Rory started out as enemies, in a storyline that served as a fantastic example of the ways in which women feel compelled to compete with one another in a patriarchal and tokenistic society. 

Eventually, though, they realise they have far more in common than they first realised. Paris is perhaps the one character in A Year in the Life who seems truly content, and who ended up where she should have. She consistently challenged Rory, who was better for it, and embodied what the show was and should always have been about: friendship.