Every “Gilmore Girls” Boyfriend, Ranked From Worst To Best

So it's been awhile since my last rewatch but so much of the show is Lorelai and the grandparents and the Stars Hollow residents talking about how Rory is SO special and SO talented and SUCH a good kid. Which leads to the narrative among a lot of fans that Rory is super spoiled (which she is in some ways, she's very financially privileged), but so much of that praise is actually pressure. Rory isn't allowed to want things or do things that violate the image of her as "perfect Rory". Any mistakes she makes are a big, big deal.

Lorelai insinuates herself into the relationship with Dean pretty early (and not in like, a healthy, mom keeping an eye on things way) and there's no room for Rory to push boundaries. But with Jess, he and Lorelai are antagonistic really early on (and I agree with the commenter below that Lorelai's whole attitude was initially pretty shitty since Jess was a teenager moving in with Luke to get out of an abusive home). So by choosing him, Rory is already violating her mom's expectations of her, and there's more room there to explore what she wants.