The hit show Gilmore Girls brought the charm of small-town life to the small screen in the early 2000s, and Rory Gilmore’s tumultuous love life found her with four different boyfriends over the course of the series. Gilmore Girls focuses on Rory and her mother, Lorelai, as they navigate the ups and downs of love and life. The women’s relationships are a central focus of the show, with romantic interests playing a huge role from the beginning. Rory takes on a few serious partnerships, giving her a rich relationship history — one that’s sparked a lot of debate over which character the youngest Gilmore should have ended up with.
Viewers meet Rory’s first on-screen boyfriend — Dean Forrester — in Gilmore Girls’ pilot episode. The series sees Rory transitioning from a studious teen in the fictional town of Stars Hollow to a student at Yale, and her relationships reflect this journey. Rory meets Logan Huntzberger, one of her most serious boyfriends, while she’s at the Ivy League school. During Netflix’s revival, Gilmore Girls: A Year in the Life, fans also get a glimpse of Rory’s most forgettable boyfriend: Paul. Throughout the original and revival, Jess Mariano also remains in Rory’s orbit. Naturally, Gilmore Girls fans have mixed feelings about who Rory’s best boyfriend is, but some are clearly better than others.
4 Paul
Played by Jack Carpenter, Paul enters the Gilmores’ orbit in Gilmore Girls: A Year in the Life and is forgotten almost immediately. He’s set up as a long-term-boyfriend for Rory, but everyone — including Rory — keeps forgetting about him. Paul is seemingly nothing more than a plot device to further Rory’s storyline, so much so that the creators don’t bother giving him a last name. Paul has a straight-laced persona, and given the invigorating — albeit somewhat unhealthy — relationships of Rory’s past, this lays the ground for her indifference to him.
Although Paul is Rory’s longest relationship, viewers see the least of him, and his boring characterization lands him at the bottom of her list of beaus. Paul is an overall good guy, and the writers may have missed an opportunity for Rory’s growth with this storyline. He plays his part well, setting a foundation for Rory’s cheating, and serves as a conduit for her past boyfriends to make appearances in the Netflix revival. Paul doesn’t deserve the way he’s treated, but his forgettable appearance does provide some humor during Gilmore Girls: A Year in the Life.
3 Dean Forester
Played by Jared Padalecki, Dean Forester is Rory’s first boyfriend in Gilmore Girls. The two meet in the show’s pilot episode, and the beginning of Dean and Rory’s relationship timeline finds the pair navigating a sweet and innocent young love. However, when Jess Mariano shows up, things between Rory and Dean quickly sour. By Gilmore Girls season 3, the two are broken up, and their final blowout showcases how toxic their relationship becomes. Dean marries someone else in Gilmore Girls season 4, but he and Rory often have trouble keeping away from each other — a fact that eventually leads Dean to cheat on his wife with Rory.
Rory and Dean’s relationship captures the comfortable familiarity of young love. His feelings for her are sincere, but he doesn’t always convey them well. He plays the dopey lover boy, constantly making mistakes for — and with — Rory in the name of love, and it works for his character. He takes his ups and downs in stride and seems to have found happiness in Gilmore Girls: A Year in the Life. Ultimately, his immaturity stops him from moving up on Rory’s list of boyfriends, but his sincerity makes him a strong choice.
2 Logan Huntzberger
Rory meets Logan Huntzberger (Matt Czuchry) as a college student working at the Yale Daily News. Their romance takes off right as Rory and Dean’s second attempt at a relationship ends, as Logan comforts her after their breakup. Rory and Logan’s relationship timeline starts as a slow burn, with each wooing the other in imaginative ways. Logan treats Rory with respect and seems to understand and appreciate her values. He even pushes back against his elitist parents, both of whom disapprove of Rory’s life choices. Sadly, however, this pompous and elitist attitude comes through in Logan’s words and actions, too.
Even with his flaws, Logan inspires Rory in a way her other boyfriends do not. She takes more risks when she’s with him, which works out for her in some cases — and creates problems in others. She and Logan still have feelings for one another in A Year in the Life, which is evident when she cheats on Paul with Logan and later becomes pregnant. There is a lot of love and an equal amount of understanding in their relationship, but at times, it lacks the maturity needed to make a college-level relationship thrive in adulthood.
1 Jess Mariano
Luke’s nephew, Jess Mariano (Milo Ventimiglia), first appears in Stars Hollow in Gilmore Girls season 2, and he disrupts Rory and Dean’s relationship as soon as he arrives. Rory and Jess’ chemistry is palpable from the start, as audiences see the standoffish Jess’ softer side come out during his interactions with Rory. The two characters really understand each other, and they find common ground in their love of literature. It’s because of Jess that Rory starts to see what she’s missing with Dean. She and Jess are a good match for one another when they meet, as Jess’ bad boy image balances Rory’s more conserved nature.
Rory and Jess’ relationship is built on respect and understanding of what love means to them, and this translates well as the series progresses. Though they have their ups and downs, every time they reunite, they do so with care. Their relationship is able to withstand their breakup in ways not seen with Rory’s other boyfriends, and it garners a loving throughline for a relationship outside of romance. This ability to love and respect each other, even in the years after the events of the original Gilmore Girls, is why Jess is the number one boyfriend in Rory’s life.
