It's true. When I watched Gilmore Girls as a teenager, I loved Jess. I just wanted him and Rory to live happily ever after. I guess he was cute, and he read a lot, and he could talk really passionately about books, and that was all I needed. Even when watching the Netflix revival, my inner teen squeed when Jess finally appeared on screen.
But I've just finished rewatching Season Three for the first time in years and years, and it's official. Jess is the worst. Like, the actual, literal worst. What was teen!me thinking? How does he have such an important place in so many viewers' hearts?
In Season Two, Jess is generally terrible to most people, but at least he is nice to Rory. He's engaging and interesting with her, even though he's also a brat, and I think their book-related conversations and 'Ernest only has lovely things to say about you' moments fuel seasons of Jess-related blinkers. Even then, he's pursuing Rory while she's dating Dean, ignoring any boundaries she tries to set because "he knows her better than that," and generally being not great. But at least they have good conversations too.
Once they get together in Season Three, he becomes actually, objectively terrible. I don't think he and Rory have a single conversation about books after they get together. They don't really have conversations about anything. Instead, we get a never-ending parade of terrible Jess behaviors.
He lies to Rory. He is rude and monosyllabic to Emily in a way that almost requires more effort than being polite, and then blames Rory for his behavior because she invited him to dinner in the first place. He refuses to do pretty much anything town-related and fun with Rory unless Dean also happens to be there, at which point he becomes possessive!boyfriend guy. He's generally aggressive and dismissive to everyone, is so cool and alternative that he refuses to get a cellphone, and insists that he's only failing school because he's way smarter than all those losers anyway.
That's not even mentioning the two worst things he does: pressuring Rory to sleep with him at Kyle's party, and then getting mad at her and shouting at her when she refuses, and then running out of town almost immediately afterwards without saying a word to Rory, even though he had a clear chance to talk to her.
Jess's behavior to Rory verges on emotional abuse. He's cold to her and ignores her, so she freaks out about what she's doing on. When she finally stands up for herself, he appears with Magical Concert Tickets and All The Affection, so she backs down and stays with him. Then he quickly goes back to ignoring her again. He's almost constantly angry, and it's always because of things that Rory did, choices Rory made, even though Rory hasn't done anything wrong, except perhaps stand up for herself.
Maybe it's a sign that I've gotten old, but I completely understand Lorelai. I despise Jess and want Rory to run.
And yes, people will excuse Jess's behavior by pointing out what a rough deal he's gotten in life, how his mother basically abandoned him in Stars Hollow. But his own unhappiness and anger with the world doesn't excuse him acting cold and abusive towards anyone else, and his past doesn't change the fact that he is a terrible boyfriend and cruel towards Rory once they get together.
The thing is, the show does kind of suggest that this relationship is a complete mess. It suggests that Rory is wrong and Lorelai is right, that Jess is an angry, messed up guy and him liking both books and Rory isn't enough to change that. Lorelai and Rory explicitly have a conversation in the car, where Rory says she doesn't want to be the girl who lets her boyfriend push her around any more, and Lorelai emphasizes how all the stuff he's done makes him a jerk. But the Season Two set-up kind of makes us want Rory and Jess to work it out. We've seen that he can be nice, at least to Rory, and it's really easy to get stuck in that shippy narrative of "it's just an obstacle to everything working out because they're made for each other." But sometimes "obstacles" are deal-breakers, and Jess's abusive behaviour is definitely a reason why they should not be together, no matter how cute they can be.
Of course, Jess grows later in the series. In Season Four, he's still terrible, coming back, telling Rory he loves her, and then running off again. Then coming back again, telling her she should ditch her family and Yale and run away with him, and leaving again when she refuses. It's only in Season Six that he becomes Wise Jess, who's published a book and notices that Logan is a jerk and shouts at Rory for dropping out of Yale. He's the guy from the past who appears and motivates her to sort her life out, a role that he plays again in the revival. It's definitely a more likeable Jess. But it's also quite a worrying shift, considering his past role in the show. This guy who was neglectful, cruel and emotionally abusive is now the person who is wise and knows what Rory needs better than Rory does? From a shippy point of view, we eat it up. But from a different perspective, it's insulting. He knows her better than anyone? He comes back to yell at the girlfriend he was so cruel to, telling her that her life is wrong, and he's the good guy in the situation? What's that implying about all the previous times he shouted at her in earlier seasons? Were we supposed to think he was right and wise then too?
This isn't to say that Rory's other boyfriends are much better. A Dean rant may be coming soon. But I always hated Dean. Jess somehow managed to be the kind of guy who seems compelling as a teenager, but it actually absolutely terrible. And it worries me how much I loved him, considering how truly awful he is.