Gilmore Girls fans have spent the last decade arguing over who Rory Gilmore truely belonged with. While her first boyfriend, Dean Forrester, was a nice enough guy initially, most fans agree that he wasn’t the right fit for Rory. Her other two main love interests, Jess Mariano and Logan Huntzberger, have plenty of fans, though Rory and Jess edge out Logan and Rory in many Gilmore Girls popularity races. While there were plenty of good things about Jess, in the end, we don’t think he was compatible with Rory. The short-lived relationship didn’t make much sense if you think about it.
Rory and Jess had incredibly different personalities
Jess and Rory were drawn to each other the moment Jess was introduced on Gilmore Girls. The moment Jess stepped off the bus from New York, he was intrigued by Rory. Rory found his mysterious nature interesting. But why? If you look at Rory and Jess as individuals, it never seemed like their personalities were well-suited to each other.
Jess was combative and vigorously against all rules. He didn’t see the point in getting an education and certainly wasn’t interested in the social life around Stars Hollow. Rory was timid and seemed most comfortable when an authority figure was telling her what to do. She was also deeply entrenched in Stars Hollow’s bustling social calendar and was largely a people-pleaser.
They had completely different plans for their future
Dean Forrester is often considered all wrong for Rory because his goals didn’t align with hers. Dean had little interest in leaving Stars Hollow. He didn’t seem to see himself as someone who could achieve great things. If Dean and Rory were incompatible because of their life goals, you could argue that Rory and Jess were incompatible for the same reason.
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Jess had no interest in college and had absolutely no future plans. Sure, he had no interest in staying in Stars Hollow, but that’s likely because he was only sent to live in the tiny hamlet as a teen. Jess had wanderlust, while Rory did not. The town’s resident bad boy wanted to figure out things as he went along, while Rory had a concrete plan for her future. The high school sweethearts likely wouldn’t have made it more than a year with Rory at Yale if Jess hadn’t bailed earlier. If we had seen more of Jess and Rory on Gilmore Girls, the cracks in their relationship would have been evident pretty quickly.
Neither was any good at communicating
One thing Jess and Rory had in common is still a strike against their long-term compatibility. Neither Jess nor Rory was comfortable communicating their needs, wants, or feelings. During the entirety of their relationship, fans watched them dance around how they felt. The duo also failed to let each other in on major life decisions or moments when they were unsure about the status of their relationship.
Jess never told Rory that he couldn’t graduate from Stars Hollow High School on time. Instead, he skipped town. Rory didn’t feel comfortable enough with Jess to tell him that she wanted to figure out how to maintain a friendly relationship with Dean Forrester. Neither Jess nor Rory trusted each other, and they only communicated that in passive-aggressive slights.
While we admit the couple looked cute together, their commonalities were pretty limited. The only thing they had in common was their shared intellectual curiosity. While a nice connection, it hardly seemed like enough to sustain a relationship in the long term. Jess and Rory didn’t make sense as a couple, and their long-term compatibility was questionable at best.
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