Though Jess captured many fans’ hearts as Rory’s boyfriend on Gilmore Girls, it can sometimes be hard to fathom why. Jess Mariano joined the cast in Gilmore Girls season 2. Introduced as Luke Danes’ nephew, Jess was sent to Stars Hollow after a falling out with his mother and generally being a troubled teenager. He had a hard time connecting with anyone, even his uncle, aside from Rory Gilmore. Jess and Rory had a lot in common, and as they started spending more time together, it became clear they were falling for one another, despite Rory still being with her first boyfriend Dean at the time.


On paper, Gilmore Girls‘ Jess and Rory fit well together. They had the same taste in music, shared the same overwhelming love of literature, and she saw his potential when no one else did. Ultimately, they were able to be themselves around one another. Jess would never pressure Rory about being the best at school or ensuring her acceptance to an Ivy League, and Rory in turn got to see glimpses of the real Jess and allowed him his space when he needed it. It was Jess’ need for space, however, that ended up getting in the way of their relationship, and ultimately led to Jess’ mistreatment of Rory while they were together.

Related: Gilmore Girls: Why Rory’s Original Ending Was Perfect

Jess Never Put Rory First In Gilmore Girls

Jess Mariano and Rory Gilmore walking in Gilmore Girls

When Rory was still with Dean, Jess did a lot to be able to spend time with her. He brought her a care package when she was home alone for the weekend, he bid on her lunch basket at one of Stars Hollow’s many town festivities to be able to spend an afternoon with her, and even tried to be cordial with Rory’s mother Lorelai Gilmore while he was helping her clean her rain gutters. Before Rory and Jess were officially together, he put a lot of effort into developing and maintaining a relationship with her, even if it was just a friendship.

But once their relationship started, Jess became scared, buckling under the pressure of being “Rory Gilmore’s boyfriend” in a town where she was practically worshiped, and he was constantly looked down upon. That doesn’t excuse his behavior, however. Jess never really made plans with Rory, even when it was something she really wanted to do. He’d show up out of the blue to make things okay between them but never took the time to explain why he’d disappeared. He failed to make her dream of a Stars Hollow High prom night come true, and never gave her a reason why.

His inability to express his insecurities left Rory feeling inadequate, as though she had done something wrong, and this was never more apparent than when he got into a fight with Dean after she stopped them from being physically intimate at a party. Though Rory always saw the best in Jess on Gilmore Girls, he never truly let her in, pushing her away when she was probably one of the few people who would understand why he felt like he needed to take on the world on his own. Jess’ refusal to confide in Rory ultimately led to their breakup, despite his later insistence that he loved her.

Jess Moved Away Without Even Breaking Up With Rory

Jess and Rory breakup bus scene Gilmore Girls season 3

Jess was a lost soul when he was introduced on Gilmore Girls – troubled, sent away by his mother, and rejected by his father at a young age. The only family member who tried to make an effort with him was Luke, and at first, that wasn’t enough, though their relationship certainly progressed throughout the later Gilmore Girls seasons. Jess’ insecurities stemmed from the fact that he felt like no one wanted him, no one cared about him, and he needed to find his place in the world.

Related: Gilmore Girls: Jess Was Too Good For Rory In The End

His leaving Stars Hollow in Gilmore Girls season 3 was perhaps not entirely unexpected – Jess needed to find and connect with his father before he could figure out who he was and whom he wanted to be. But in doing so, he ran away from those who truly did care about him, flaws and all. Jess leaving Stars Hollow without giving Rory an explanation was a cowardly way out of a relationship that was getting serious and could have turned his life around. Rory deserved better, and it wasn’t until Gilmore Girls season 6 that Jess became someone who could have been an equal participant in their relationship, though it was too late by then.

Their Chemistry Was Incredible At First

Jess and Rory standing outside on Gilmore Girls

Despite all that trouble in their early relationship, Jess is still arguably Rory’s most popular love interest. This is most likely due to their chemistry – Jess and Rory’s first interactions were so indicative of who they both were, apart and together, showcasing their shared love of the written word and having the same sense of humor. Despite his flaws, Jess and Rory shared a genuine connection, one that felt more natural and instinctive than her relationships with both Dean and Logan. Jess was convinced that he and Rory belonged together, that he knew her better than anyone, and he held this belief with such conviction that the audience could easily believe it too.

Even after Netflix’s Gilmore Girls: A Year in the Life revival, Jess seemed to know her better than anyone. Rory’s affair with Logan was a regression back to her affair with Dean in Gilmore Girls season 4. But Rory’s scenes with Jess in A Year in the Life, on the other hand, once again proved how well they understood each other. He helped her see her potential, reminded her of everything that she was capable of, and returned the favor of how she’d supported him all those years ago. Ultimately, they make each other better. Jess and Rory’s chemistry and compatibility have never waned since their first meeting on Gilmore Girls, ensuring Team Jess’ enduring popularity.

Next: The Two Planned Gilmore Girls Spinoffs That Never Happened

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