Jess from Gilmore Girls is the Worst

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.

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 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 wrong. 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.

12 Replies to “Jess from Gilmore Girls is the Worst”

  1. Lars Sjöström says: Reply

    I think that it’s quite normal to like unhealthy behaviour and unhealthy relationships in fiction.

    In an old Disney. When Daisy Duck and Donald Duck are on a date, Gladstone Gander shows up in a more fancy car, Daisy immediately switch to Gladstone. Donald empties his bank account to buy an even fancier car(despite poor income and being lone foster father to three boys). When it has ended in disaster, Daisy only blames Donald and Gladstone, despite that she didn’t have to switch date. At the time I laughed at it. Nowadays I think that Donald should have broken up this unhealthy relationship and Daisy rethink her priorities.

    When I read marvel comics it was very much the same thing. Rogues on and off relationships with Magneto, Gambit and Joseph was the most interesting.

    I guess that we like to read about/watch unstable and/or unhealthy relationships above the better ones, to prepare ourselves for the day when we might end up in one ourselves. Like a scary story might be a preparation for dangerous or traumatic experiences in the real world.

    1. I think that’s an interesting perspective, although it becomes a problem when we romanticise unhealthy relationships in fiction and then potentially emulate them in real life. I know the sheen first wore off Jess for me after I dated someone who treated me like Jess treats Rory… watching Gilmore Girls didn’t change my perspective on real-life relationships, but real life experience certainly changed how I felt about stories afterwards.

      1. Lars Sjöström says: Reply

        Good points. When I wrote prepare ourselves, I meant that we might instinctively need to think about unhealthy relationships, even if we doesn’t realize that they are unhealthy. But when we experience an unhealthy relationship, we have thoughts to relate a real unhealthy relationship to. Which in no way contradicts reevaluating the fictional unhealthy relationship.

        Another interpretation I get when I am writing this, is that we might be drawn to the fictional unhealthy relationships for the same reasons that we might end up in one in real life. The wrong people can be very nice to be with when it suits them, and then one is left longing for that they shall be so again. Maybe it is the feeling we are supposed to have when someone is gone for a while and the realtionship shall continue upon their return. An instinct that some people abuses.

        Life has changes my perspectives on fiction as well, and sometimes I really wonder why the writer described a bad relationship as good.

  2. Lars Sjöström says: Reply

    I think that it’s quite normal to like unhealthy behaviour and unhealthy relationships in fiction.

    In an old Disney. When Daisy Duck and Donald Duck are on a date, Gladstone Gander shows up in a more fancy car, Daisy immediately switch to Gladstone. Donald empties his bank account to buy an even fancier car(despite poor income and being lone foster father to three boys). When it has ended in disaster, Daisy only blames Donald and Gladstone, despite that she didn’t have to switch date. At the time I laughed at it. Nowadays I think that Donald should have broken up this unhealthy relationship and Daisy rethink her priorities.

    When I read marvel comics it was very much the same thing. Rogues on and off relationships with Magneto, Gambit and Joseph was the most interesting.

    I guess that we like to read about/watch unstable and/or unhealthy relationships above the better ones, to prepare ourselves for the day when we might end up in one ourselves. Like a scary story might be a preparation for dangerous or traumatic experiences in the real world.

  3. Oh my goodness, I agree with your whole post! I felt exactly the same way back then and am horrified now.
    All Rory’s boyfriends were terrible. And I have the same thing with Dean. I liked him at first but started disliking him very quickly.
    Rory, in general, makes some very disappointing choices in the original run of the series and I was very disappointed to see that in the revival they seem to have distilled out only Rory’s terrible qualities.

    1. I feel like Dean got a raw deal in S2 and 3, so that Jess would seem far more suitable for Rory in comparison… but even before then, he was always pretty controlling. I really hate how they present him as the guy who’s always “safe” and comforting for Rory.

  4. Oh my goodness, I agree with your whole post! I felt exactly the same way back then and am horrified now.
    All Rory’s boyfriends were terrible. And I have the same thing with Dean. I liked him at first but started disliking him very quickly.
    Rory, in general, makes some very disappointing choices in the original run of the series and I was very disappointed to see that in the revival they seem to have distilled out only Rory’s terrible qualities.

  5. THANK YOU! I really despised Jess, although he was better in season 6 and the revival.

  6. 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?

    BLESS THIS POST.

    When my rose-colored Jess glasses fell off, that’s when I knew I was truly old. I do think that Jess is a really compelling character and I am really fond of him (especially his storylines with Luke), but I am just so 100% over him as a love interest for Rory. I also think that prioritizing Rory’s POV about Rory/Jess, and looking beyond the “Jess is tragically brooding over Rory!” angle, is really important. When I was young, I was so frustrated that she didn’t seem more moved by his declarations toward her in season four, and now I’m just like, “NO WONDER, DUDE. Their romantic relationship was terribly unreliable and he literally kind of forced himself on her and then left town without them ever talking about it or even having another serious conversation; she doesn’t want to go there again, and who can blame her??”

    1. Haha, I’ve been seeing your anti-Rory/Jess posts on tumblr, and was like “oh, but, I like Jess… :(” until I got there with my own rewatch. HOW IS HE SO AWFUL? Literally just got to the “run away with me, Rory!” episode, and I’m not looking forward to the anger it’s bound to inspire.

      I feel so old. 😛

  7. This is such a relief to see. I came late to GG, having only seen snatches of it as a teenager, and binge watched it so I could join my friends in watching the revival. They set me up with Jess love and when I watched the series, I was taken aback by how my mature, feminist, well-adjusted friends could praise a character that I saw as abusive, selfish and just pretty disgusting all around. I quickly became aware that my dislike of Rory/Jess was pretty unusual in the fandom. I have wondered whether this is due to watching the series as an adult as opposed to as a teenager; although I know that teenage me would have been really unimpressed with Jess, too, I imagine that for many teenagers, Jess would have been an appealing ‘bad boy’ character.

    That’s not to say that there weren’t moments in which I sympathised with Jess, because there were, and I was relatively invested in his arc with Luke, but I HATED him with Rory. For all the reasons you’ve so well articulated.

    I also really disliked him in his brief reappearances later on, as well – with the single exception of his final one in… series 6, I think it is, when Rory goes to the book launch he invited her to. In that one, I sympathised with him and felt that Rory did treat him unfairly. But in his other cameos, I was infuriated and disgusted by his behaviour, e.g. his selfish ‘I love you’ while fleeing; him pressuring her to abandon her family and her studies (two things that are so important to Rory) and run away with him, then, again, abandoning her when she didn’t conform to his expectations of her.

    One of his worst moments, however, in my opinion, is one in which most people seem to praise him. I certainly didn’t find him to be a “more likeable Jess” in this scene. The scene where he has a go at her for daring to make choices that deviate from his image of her, where he rebukes and belittles her for taking time off from Yale, the utter hypocrisy of it, given the last time he visited and tried to convince her to actually drop out of Yale completely, his absolute arrogance in insisting that he knows her better than anyone, when he hasn’t seen her or spoken to her in a long time and knows absolutely nothing about her life or who she is… I absolutely hated it, and I really don’t understand why so many fans seem to see it as romantic or lovely or something.

    I do recognise, of course, that everybody involved in those couple of scenes – Jess, Logan and Rory – all behave badly, but to me, Jess just stepped over so many lines and showed Rory such disrespect, such a lack of empathy or compassion, such arrogance and cruelty in making her feel so small and like such a failure, when he had absolutely no idea (and just didn’t care) what her reasons were or how she was feeling, that it made me furious to watch.

    And for me, it really echoes back to a couple of crucial things in that ship: Jess did not respect Rory’s autonomy or her consent. He held her to an unfair standard in which he expected her to live up to the image he had of her, and he was cruel to her if she dared to step off that pedestal and make her own decisions. He repeatedly refused to respect her choices – or her consent, as in the horrible scene at Kyle’s party that you mentioned – or accept her for who she was.

    Unfortunately, putting Rory on a pedestal and giving her a hard time if she steps off it, and belittling or not respecting her choices, is something that a few other characters (Dean, Lorelai) tend towards when it comes to her, as well, though perhaps not in such an overt or unpleasant manner. (And I do think that Rory treated Dean badly, too, and also that his character was altered significantly after series 1 to make room for Jess.) This is something that, for all his faults, I do feel that Logan differed on. He may not have agreed with some of her choices, but he accepted that they were her decisions and respected them. (I’m ignoring the revival, because I just can’t even get started on whatever the hell was going on with them there.)

    Sorry for that rant! Anyway, I just wanted to say that I really appreciated this article! 🙂

    1. Thank you! Even though I’ve been marathoning through the series, I didn’t see the connection between Jess’s “run away with me” moment in S4 and his “why did you quit Yale??” rant in S6 until you just pointed it out. You’re right that he’s not even trying to get her to be herself and do what’s right for her, but get her to fit into whoever he thinks she should be at the time.

      You make a good point about Rory’s autonomy too. I’ve just finished watching the beginning of S6, and I can’t believe how melodramatic the “good” characters get over Rory taking a break from Yale. When I saw it as a teenager, it seemed like a total disaster for her, but now I’m watching it having actually been through college, lots of people take a semester or a year out to help themselves to refocus and regain their motivation. Maybe if someone had actually listened to what Rory was thinking instead of berating her for not being herself, things would have gone better for everyone.

What do you think?