Jess Was Actually A Horrible 'Gilmore Girls' Boyfriend — 8 Reasons He Was Toxic For Rory

For a little refresher: Rory's first-ever boyfriend was Dean Forester, a blonde-haired teen who was chivalrous and treated her with respect. Not to mention, he spent months building Rory a vintage car for their anniversary! As a couple, they definitely weren't perfect, but whose first relationship is ever all sunshine and rainbows?

Then came Jess Mariano, Luke's troubled nephew, who went to live with him in Stars Hollow. He entered the Gilmore Girlsworld while Rory was still dating Dean, and in our eyes, he proved to be toxic from the start.

Jess immediately set his sights on Rory and, in the process, began sabotaging her relationship with Dean. First, he stole the bracelet Dean had made for her, poked fun at their relationship overall, and sparked plenty of fights between them.

Yes, Rory seemed to have a fondness for Jess's more aloof and mysterious nature. But who can blame her? Even though most teenage girls find "bad boys" endearing, that doesn't mean they're good news!

Then, following Rory's breakup with Dean, she and Jess quickly began dating, but their relationship wasn't nearly as wholesome as her partnership with Dean for various reasons. They might've been intellectual equals who pushed each other and had undeniable chemistry. However, their dynamic simply wasn't healthy.

Jess wasn't able to open up or communicate his feelings to Rory, likely due to his childhood trauma, which left her constantly questioning the state of their relationship. He also blatantly disrespected Rory's family, showed no appreciation to Luke for taking him in, and failed high school, not because of his intelligence, but merely because he didn't show up or put in any effort!

The worst Jess moments, though, were undeniably when he tried to pressure Rory to sleep with him at a party, causing her to start crying and run away, and when he left Stars Hollow and totally ghosted her. Plus, when Jess later returned, he wanted Rory to upend her life and run away to New York with him!

We learned in subsequent seasons that Jess ultimately got his stuff together, became an author at a small publishing house, and wrote his own book. It's true that people can grow, and no one has it all figured out during their teen years. Nonetheless, I still don't believe Jess was the right partner for Rory, especially if you compare their relationship to her time spent with Logan Huntzberger.

It was season 5 when Rory first met Logan during her sophomore year at Yale. Sure, he could be a bit rebellious and flirty, but once he and Rory began to get serious, he proved to be a very witty, supportive, and charming young man.

Jess, on the other hand, usually acted in his own self-interest, had a hard time regulating his emotions, and would lash out, leaving Rory to defend his actions.

So, if we had to rank Rory's boyfriends in order of who she should've ended up with, the list would be as follows: Logan, Dean, Jess. Apologies to the Jess stans, but toxicity can be a cycle that repeats itself, and after Rory and Jess's tumultuous relationship, we believe she shouldn't go there again. But I guess we'll have to keep our fingers crossed and pray for another Gilmore Girlsreboot...