Since I maligned Jess a couple of weeks ago, it seems only fair to turn my attention to Rory's other high school boyfriend, Dean.
And god, I hate to say it, because I've always hated Dean, but... I think he may be a better boyfriend and person in general than Jess. I know. That's more of a statement of how awful Jess is than anything in praise of Dean, but it still feels wrong to say.
Dean does have some good qualities, as a person and as a boyfriend. I liked how he comforted Rory during her breakdown mid-Season 4. That was nice. And, you know, he's hardworking. He can rebuild cars, and he makes one for Rory. That's pretty cool. And he happily read books that Rory recommended and talks about them, because his personality is retconned to make Jess seem more likeable in Season 2.
But while Jess is cruel and nigh emotionally abusive by being so distant, Dean is worryingly controlling. The first sign is that godawful Donna Reed episode, where he talks about how nice and wonderful 1950s housewives are, and Rory ends up roleplaying one to make him happy. No wonder he ended up being unhappy in his own marriage and idealising Rory. No actual woman could live up to that ideal, so his highschool girlfriend became it in his head.
And there are many moments in Season 2 which are demonstrably not okay. Like the bracelet incident, where Rory is terrified of telling Dean that she lost the jewellery he made her, even though it was an accident, and she's clearly distraught. She shouldn't be so afraid of telling her boyfriend that she lost a piece of homemade jewellery after a year of daily wear, but no-one stops to point out how unhealthy her panic is, not even Lorelai. Or there's the laundry incident, where Dean refuses to understand that Rory might want to spend some time alone, and definitely can't stand the idea that she might want to spend time with people other than him.
In Dean's defense, Rory's behavior towards him in Season 2 echoes Jess's eventually behavior in Season 3, as she ignores him, forgets to call him, and generally keeps him on the hook. But when she's in a car crash, he's not worried that she was in a car accident and ended up in the hospital. He's just furious that Rory got in a car with Jess at all, and his forgiveness for his girlfriend breaking her arm is treated as some great kindness on his part. He hates Jess, but not because of any particular incident. He hates him automatically, because Jess and Rory get along. In Season 2 and 3, he's either bored by Rory's interests or yelling at her for not acting how he would like her to. And let's be fair, Rory is being a terrible girlfriend, but that's a reason for Dean to break up with her, not for him to control her. She often seems more trapped by Dean than in a relationship with him.
And then, of course, Dean marries Lindsey after being together for about half a year, and then stares moony-eyed across Stars Hollow at Rory, hooking up with her because he likes her more than Lindsey, and then shouting at Lindsey and making her feel terrible afterwards. Lindsey runs around, desperately trying to learn how to cook and be the perfect Donna Reed-esque wife so that Dean will love her, and none of it is good enough for him, because no one can be as perfect as Rory in his mind. Yet he doesn't intend to actually end his marriage with Lindsey, because he still needs the perfect life on the hook, the wife trying so hard to be domestic enough to please him and the pining over perfect Rory on the side. And when his actions end his marriage anyway? Well, that's Rory's fault for not being perfect.
Honestly, this Gilmore Girls rewatch is revealing to me that everyone is even more terrible than I remember them being, and desperately hoping that we're not supposed to like any of Rory's high school boyfriends, because while they might be realistic, they're terrible guys to idealize. Rory might see Dean as the boring-but-reliable guy, but over and over again, he shows himself to be patronising and controlling, and uncomfortable with the idea that Rory might have a life or a future that's bigger than his or him.