Writing: Heather Taylor-Singh @htaylorsingh
I started watching Gilmore Girls in 2014 when it dropped on Netflix. I was far too young to be watching television when the gals made their debut on the CW in October 2000 (I was two years old). As I binge-watched the show throughout high school, I fell in love with the mother-daughter duo of Lorelai Gilmore (Lauren Graham) and Rory Gilmore (Alexis Bledel) and tried to keep up with their rapid dialogue and wildly unhealthy eating habits. 20 years later, we’re still talking about these dynamic women and the lives they lived. Gilmore Girls is genuinely heartfelt and serves as the ultimate comfort show—it feels like a familiar friend giving you a warm hug (something we could all use a lot of right now).
While the heart of the show was Lorelai and Rory’s relationship with one another, I, like so many, was always intrigued by the suitors in Rory’s life. From her flawed first love, Dean Forester (Jared Padalecki), to an ever-brooding Jess Mariano (Milo Ventimiglia), each love interest had an effect on Rory… and me, if I’m being honest. While she wasn’t always the best character (see: the entirety of Season 6), the question of Rory’s “best” relationship dominated the show’s seven seasons, and we’ll be unpacking them in this list, a definitive, yet completely subjective ranking of Rory Gilmore’s boyfriends.
Dean is tall, handsome and has adorably floppy hair. He is Rory’s first kiss, first boyfriend, and later on, first sexual experience. Rory and Dean have a sweet relationship at the beginning— cue their adorable first kiss at Doose’s Market —but it all comes to a crashing halt when Dean breaks up with Rory because she doesn’t verbalize that she loves him. He’s constantly threatened by the other men in Rory’s life and asserts his dominance whenever he can, eventually leading to their public breakup at an all-night dance marathon. Seasons later, Dean shows his true colours by cheating on his wife with Rory, eventually ending his marriage.
Dean’s constant insecurities controlled their relationship, and propelled their final breakup. He didn’t have much ambition for a life outside of Stars Hollow, which was the complete opposite of Rory. Dean loved her, but his love was conditional. Rory and Dean never brought out of the best in each other and outgrew one another as they went in different directions.
Looking back, Tristan was a mix of Jess and Logan; he was moody and emotionally unavailable, wealthy and arrogant. Plus, he was played by the ever-so dreamy Chad Michael Murray. The dynamic between Rory and Tristan was interesting because she wanted nothing to do with him, yet he was always inserting himself in situations that didn’t concern him, furthering Rory’s distaste for him. It’s clear he was hiding his crush on Rory, but went about it in the most childish way, by judging every move she made and making fun of her virginity (who could forget when he nicknamed her “Mary?”) They had minimal sweet moments, like a kiss at Madeline’s party when emotions were running high, but Rory deserved better than a guy who couldn’t be honest about his feelings and thought PJ Harvey was a guy. It was admittedly sad when he got sent away to military school, abruptly ending any connection they had. Miss you, Tristan!
Did you forget about this almost-relationship? Marty was the inoffensive nice guy who was borderline boring, but saw Rory as his equal. They had fun banter, were comfortable around each other and were probably the only two students at Yale who weren’t oozing with privilege. Marty was friend-zoned by Rory because she had feelings for Logan. We don’t see Marty much throughout the series (and he didn’t even have a last name), but it’s clear he genuinely cared for Rory, and was the most unproblematic love interest for her. Except for when he hid their friendship from Lucy in Season 7 and acted skittish whenever Rory was around.
There are mixed feelings surrounding Rory and Logan’s relationship. Logan embodied a stereotypical, selfish, privileged rich boy. His apathy towards school and eagerness towards partying was frustrating, but it made him fun! Logan brings Rory, whom he nicknames “Ace,” out of her shell, convincing her to live on the edge. He brings her to secret society parties, makes grand romantic gestures and eventually becomes less of a playboy. Logan is Rory’s main relationship in university, and while Rory made Logan a better person, their relationship sometimes feels one-sided.
Logan wasn’t strong enough to break away from his powerful, rich lifestyle to be with Rory. They came from two different worlds and Logan’s love for Rory would only go so far because the Huntzberger family had other plans for his future. Not to mention, when Mitchum, Logan’s father, told Rory she wasn’t cut out for journalism, leading to her dropping out of Yale, which Logan put minimal effort into mending. As Rory gets back on track, she’s less willing to pick up the pieces of Logan’s opulent behaviour. Their relationship was fun to watch, but Rory and Logan didn’t have the stamina to last in a committed, healthy relationship.
Jess is Rory’s intellectual equal. They bond over classic literature and share a wittiness reserved only for the two of them. There is an unspoken deeper connection between the two. But Jess is going through it: his family life is unstable, he’s not doing well in school, and he’s constantly causing trouble, whether it’s stealing garden gnomes or starting fights at school. Most of the time, he is emotionally unavailable and fails to care for Rory’s emotions, especially in a grim scene where he almost sexually assaults Rory at a party. He didn’t have much to offer Rory or Stars Hollow, so he abruptly leaves town without telling her, which was heartbreaking.
After Jess’ initial departure, we see fragmented moments of him. He comes back in Season 4 in an attempt to win Rory back. Jess returns in Season 6 as a whole new man. He’s mature, emotionally stable and he’s written a book. He makes Rory rethink her decision to drop out of Yale and challenges her relationship with Logan. Originally, Rory brought out the best in Jess, but when they reconnect in later seasons, the roles are reversed. Their timing was always off, but here’s hoping they get back together one day.
More like this: