‘Gilmore Girls’: Was Rory Gilmore and Jess Mariano’s Relationship Toxic?

Twenty years after Gilmore Girls premiered, fans of the series are still discussing which of Rory Gilmore’s three main love interests was the best fit for her. While few people believe Rory’s first boyfriend, Dean Forrester, was her everlasting love, fans are a bit more divided when it comes to Jess Mariano and Logan Huntzberger. Jess has a ton of fans, but he and Rory’s relationship was pretty toxic if you think about it.

Jess’s initial pursuit of Rory was toxic and mean-spirited

Jess’s pursuit of Rory began pretty much the second he moved to Stars Hollow. While he never mentioned why he’s so interested in her, he certainly made it his job to pursue her. His approach, however, was incredibly mean-spirited.

RELATED: ‘Gilmore Girls’: Is Jess Mariano Rory Gilmore’s Luke Danes?

First, he went out of his way to make fun of Dean and Rory’s relationship. He stole her bracelet, caused fights between the couple, and tried to make Rory jealous of Shane. At times, it was hard to figure out if Jess was interested in dating Rory, or if he was just interested in seeing if he could break up Rory and Dean, who, at the time, seemed like the perfect, wholesome couple.

His inability to communicate made Rory question everything

Once Jess did get the girl, his inability to communicate made a serious relationship almost impossible. He left Rory questioning everything, including whether he actually liked her. When he found out he couldn’t go to prom, he tried to pressure Rory into having sex, then left town without saying a word, recalls Romper.

Milo Ventimiglia as Jess Mariano and Scott Patterson as Luke Danes in 'Gilmore Girls: A Year in the Life'
Jess Mariano and Luke Danes in ‘Gilmore Girls: A Year in the Life’| Netflix

After the relationship was over, he showed back up repeatedly, just to leave Rory hanging again. He acted angry that she existed. He told her he loved her, and then took off and made it impossible for her to reach him. Jess was the one partner Rory had that completely failed to consider her feelings. Even Logan, while immature and self-involved, managed to consider Rory’s feelings most of the time.

He overestimated his own abilities

Jess was smart, there is no question about that, but he consistently overestimated his own abilities. He also overestimated the depth of other people’s feelings for him. When he returned to Stars Hollow in season 4, he expected Rory to simply run away with him to New York, after he left her without even saying goodbye. Two seasons later, he suggested he knew Rory better than anyone else.

RELATED: ‘Gilmore Girls’: Michel Gerard and Jess Mariano Had A Couple of Things in Common

While Jess grew into a responsible and reasonable adult, he had a really difficult time reading a room. Rory suffered because of it. All in all, he was pretty toxic as a teen and young adult. That doesn’t mean he’d be the same in a relationship as a grown man, though.