It’s Jess.
I’m sorry to say it, but it had to be said.
I have been staunchly team Jess for many years. His chemistry with Rory cannot be argued, nor can it be argued that the episodes featuring Jess are some of the best of the series. Despite having both feet in his corner, during my latest rewatch I couldn’t help but notice that Jess was actually a terrible boyfriend.
What did he do to make me change my mind? And what brought upon this switch?
- . FLAKY
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In the season 3 episode “Face-Off,” Jess tells Rory he will call, but doesn’t.
He is the king of nonchalant: he invented it.
If the show took place in 2026, he would leave her on read and then like her Instagram story. He’s that kind of guy—the kind who breadcrumbs a girl despite the effort he took to win her over, and the kind who cares more about his hair than he does about giving his girlfriend a call-back. Rory rightfully gets fed up and goes out without him. While she’s out, she must explain why Jess isn’t there, humiliating herself by downplaying his Bad Boyfriend Behaviour (BBB, if you will). When he does eventually show up, (at the back of the building mind you)he talks around the issue and presents her with concert tickets.
When I was younger, I thought this was devastatingly romantic. Sure, he may not be pleasant to anyone, not even always to his own girlfriend, but he has a car and concert tickets! Now I think Rory would have been better off going to a concert with Kirk and Babette. You do not have to accept the bare minimum just because a guy has great hair. I know it’s a crazy concept, but it’s true.
By being flaky, Jess proves he does not value Rory’s time, meaning he cannot truly value her.
- . MOMMY ISSUES
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Jess and Rory’s mom, Lorelai, famously do not get along. First, he leaves a dinner party that was in his honor, then steals Rory’s bracelet that Dean (her boyfriend at that time) made, AND THEN, cherry on top, he crashes the car Dean built for Rory, hurting her arm. None of these instances portray him as a stand-up citizen, and they are all sound reasons to dislike your daughter’s boyfriend, so Lorelai never truly gave Jess a fair chance. She had her mind made on him so that she was unable to know him as Rory did, but Jess certainly didn’t do his part to develop a friendly relationship with her.
He avoids her when possible, and when it isn’t, he replies in grunts and leaves as soon as the door opens. Frankly, he’s rude. Gilmore Girls is about the close relationship between the Gilmore girls. He knows that Rory and her mom are inseparable; he knows that her mom is important to her, but he does not care about what is important to Rory. Jess only cares about what Jess cares about. He once again proves that he is not serious about their relationship by dismissing what is important in his girlfriend’s life.
Don’t give in to someone who won’t give.
- . COMMUNICATION? NEVER HEARD OF HER
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Jess is a rebel without a cause—the poor man’s James Dean. He constantly broods in his leather jacket with no place to put his grief, and the bad boy act becomes exhausting when he refuses to talk about his issues. It’s almost like he would rather be in pain than communicate, and that becomes Rory’s problem when he takes those issues out on her.
Jess’s outbursts cut deep because they go unexplained. In the season 3 episode “Keg! Max!“, Jess doesn’t tell Rory that he’s been kicked out of school, resulting in him being closed off and rude the entire night. Rory attempts to cheer him up, understand him, and explain for him, but her efforts fail. They end up alone in a room, and he continues to kiss her despite her asking him to stop. When he does stop, he doesn’t apologize. This was his worst moment; the moment Jess claims his place as the worst Gilmore Girls boyfriend. Instead of communicating with his girlfriend, he takes his issues out on her.
Communication is the most important aspect of any relationship, and if you don’t have that, the relationship does not have its second leg to stand on.
- . MATURITY
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I think I’ve changed my mind on Jess because I am no longer a 15-year-old girl.
A nonchalant bad boy is not the kind of person I romanticize. Does a girl choose to suffer in love for passion, or for the chance to date the hot guy with a car? To feel chosen? I don’t choose that because I want to be respected, and I think that comes with getting older. Through maturing, I can recognize the kind of guy who would break my heart, and I no longer find it thrilling: I find it irritating.
Jess is not a good boyfriend; he is the textbook example of a bad one. He made for good television, but he did not make for a good partner.