A Definitive Ranking Of Rory Gilmore’s BFs, According To A Therapist
Spoiler: Dean’s not No. 1.
Gilmore Girls may have ended back in 2007, but the show is still everywhere, appearing constantly on Netflix’s recommended list and TikTok FYPs — whether it’s a video of Jess over-enunciating “Yale” or one comparing Rory and Logan’s relationship to Taylor Swift’s “Champagne Problems.” Gilmore Girls fans still are not over what went down between Rory Gilmore and her three boyfriends: Dean Forester, Jess Mariano, and Logan Huntzberger. Her romances are huge plotlines in the series — and fans and haters alike have strong feelings about all of them.
With so many conflicting opinions, it’s hard to know who deserves the title of Rory’s Best Boyfriend. Who’s the most supportive? The most compatible? The most capable of having a healthy relationship? Luckily, couples therapist Kayla Sammons at Millennial Life Counseling knows how to rank ’em.
But first, it’s important to look at the type of partner Rory is. Although she has her flaws (like shirking all forms of accountability and never acknowledging her privilege), she isn’t typically a bad girlfriend — even if she does occasionally kiss guys she isn’t dating. “Rory has a secure attachment style,” Sammons, LMFT associate, tells Elite Daily. “She is comfortable being with her partner and apart from him.” That’s a good start to building a lasting relationship.
Rory’s attitude toward dating might also explain her variety of boyfriends — sporty and possessive, moody and literary, and rich and witty. But of these three, who is the best boyfriend to her? According to Sammons, these are how Rory’s boyfriends stack up, from worst to best.
Is there such a thing as a healthy first boyfriend? Not in the world of Gilmore Girls (except for you, Dave Rygalski, you deserved better). Dean is the quintessential jock who falls for the girl he sees reading in the park. But what starts off as a sweet romance leads to some less-than-stellar boyfriend behavior. “Dean seems to rely on Rory for his well-being and can make her feel responsible for his feelings,” Sammons says.
Throughout the course of their relationship, Dean reveals he has an obsession with Donna Reed-esque housewives, lacks ambition (while feeling threatened by Rory’s), acts possessively, starts a fight, and breaks up with her because she doesn’t say “I love you” back right away. “He feels threatened and jealous of others who get close to Rory, leading him to be somewhat demanding of Rory’s time,” Sammons says. (Not to mention, he later cheats on his wife with Rory, which they both seem to have zero qualms about.)
In any relationship, these traits are red flags, but Dean’s constant demands of Rory make their relationship hard to root for. He gets annoyed with her when she spends too long looking for books and angry when she cancels plans to work on her Harvard application. Plus, his you-owe-me attitude when she asks him to wear a tux to her debutante ball is the opposite of sweet. “He puts Rory and her dreams down if they get in the way of his time with her, which he feels he deserves,” Sammons says. Dean’s loyalty is one bright spot in their relationship, but it doesn’t quite make up for the rest of his toxic behavior.
Jess is a fan-favorite. He’s broody and cute, and his soft spot for Rory makes him the perfect prototype of an angsty teenage bad boy. He has his sweet moments, too — like when he borrows one of Rory’s books and annotates it for her, or when he encourages her to go back to Yale after she drops out. (“Why did you drop out of Yaaaale?”)
But he has his problems, as well. He forgets to call Rory when they had plans, gets upset when she doesn’t want to have sex, and leaves town without saying goodbye. Despite Jess and Rory’s chemistry, their romance wasn’t exactly healthy, according to Sammons.
“Jess is unpredictable and difficult to read throughout his interactions with people,” Sammons says. This becomes clear when he fights with Luke Danes (his uncle), Lorelei Gilmore, and even Rory. “He shows an inability to regulate his emotions, and he has a strong fear of rejection, which makes it difficult [for him] to trust others.”
Considering how un-involved Jess’ parents are (which leads him to move to Stars Hollow and live with an uncle he barely knows in the first place), this emotional baggage makes perfect sense. However, that doesn’t mean it’s the foundation for a sustainable partnership. “Rory wants connection, love, trust, and honesty, and Jess struggles to give that to her since he cannot provide those things for himself,” Sammons says.
The silver lining? Throughout the series, Jess continues to evolve, working through his anger problems and even pursuing his dream career by writing a novel. Though the duo doesn’t get back together in the reboot, it’s clear there are some unresolved feelings there. It’s no wonder that fans are hoping he’ll be the one to step in and help raise Rory’s baby, just like his uncle did for Lorelei.
According to Sammons, Logan is Rory’s best boyfriend — and it’s not just because he calls her Ace. “Logan and Rory both show signs of high self-esteem, which helps them feel secure in themselves and their relationship,” she says. “Rory feels safe and excited by Logan and his unpredictability, while also knowing she’s safe with him.” (Rory wouldn’t have jumped off that ledge holding an umbrella with just anyone.)
Their relationship started off as an FWB situation but progressed into something more serious. Sammons identifies this as a good sign — *not* because all situationships should become full-blown relationships, but because they were both able to evolve together. “Rory is able to self-reflect and communicate her need for more from a partner,” she says. “Then, they both take a chance on one another not knowing if it [will] work, and that risk is what relationships are all about.”
Though their relationship has some hiccups (like that time they steal a yacht), they’re consistently willing to trust and support each other. Not to mention, Logan’s always willing to go for bat for Rory when his family members make their disapproval known. They grow together at the same pace, making their relationship one of Rory’s healthiest, even if Rory ultimately rejects Logan’s marriage proposal at graduation. Though the Gilmore Girls reboot puts them in a sticky situation — both of them cheating on their respective partners with each other before going their separate ways — he still holds the title of Rory’s Best Boyfriend.
There you have it: the definitive ranking of Rory’s boyfriends, from worst to best. (Team Jess for life, though.)