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.

omg, i LOVE this read, thank you so much! i always feel like i've analyzed Gilmore girls to death and then someone always comes along with a terrific take that makes me reevaluate everything. this is phenomenal and i totally agree with you

Lorelai's behavior with Dean in season 1 and even afterward in season 3 is sooooo problematic. She wanted to be besties with him which was so gross. There are so many issues with them idek what to say lol

There are a lot of comments here calling Jess rapey but like... i don't think so? "what Rory wants" is so important and even the scene in Kyle's bedroom the dialogue doesn't really read as people who don't sort know where they stand. Jess was definitely acting out of line bc his school breakdown but earlier episodes were pretty strongly implying things

haha when I first watched this show I was a teenager and I was like "Lorelai is great! Rory is whatever!" but as an adult Lorelai's parenting horrifies me.

I don't want to make excuses for Jess in that scene because I think it was just unacceptable. But I do think Rory's interest and her desire for him (overall, not in this scene) is way more authentic than we ever saw with Dean or most of her other love interests. ASP has some weird takes on sexuality generally, but Rory is so...watched and monitored by the adults in her life, she doesn't get room to feel out what she likes. Like the whole idea that her first time is supposed to be perfect is really fucked up to project on her, Lorelai of all people should know that.

i love this!! i always think jess and rory met at the wrong time bc he had to calm down and go through his shit and rory needed to grow up. they were never quite compatible or on the same page as teens bc jess wasn't able to communicate and rory didn't know who she was, and i think a big part of that is the suffocating presence of lorelai and that town. jess needed to be grounded and rory needed to be free.

I agree with this because the Jess that came back later on was so good and so put together. The fact that he had his life together and Rory didn’t was this great turn of events in the show and it meant something that it was him telling her to get her shit together and go back to school.

right?? i loved that about him. he really did grow up, and it was great that he even outgrew rory. i do love them a lot bc i believe they can challenge one another (when rory pulls her head out) and milo/alexis have great chemistry, but i also just enjoy his character development outside of the ship. he got shat on and he grew despite it.

the fact that he was telling her to get her ass back to school was so great considering he didn't value school for himself at all. (i think it just goes to show he understands rory and she's not rory unless she goes back to school and kicks its ass.)

It was that rarely seen character growth. Of course it all happened off camera, but it still get earned. Like Jess was at his worst in season 4, and that moment was like a kick in the ass so he could only go up from there. It even made sense that Rory had sort of devolved too. They’d flipped roles.

The show always sort of gave the impression (to me) that Rory left impressions on people. Like made them want to be better. Which is why I’d kill to see other characters from her past show back up and be better? I used to love the fan fics of Tristan rebelling against his family and joining the military because military school was good for him.

They did so well with Jess, I kind of wish they’d do it with other characters.