why do you ship jess/rory?
Hmm, I have a pretty complicated relationship with this couple mostly because I feel like the high points of Gilmore Girls have always been distorted by bad writing (even with Luke/Lorelai too).
But I prefer Jess over all the other guys because he loved her when it counted. He wouldn’t humiliate her with a public breakup like Dean did (twice), he broke up with his girlfriend before starting something with her (*throws shade at Dean again), and he would rather she follow her dreams than be with him (ok Logan). And even though he struggled a lot with expressing it and even though a lot of his mistakes were rooted in high school boy level immaturity, the development he underwent by the end of season six shows how much he progressed. (I’m REALLY into character development, in case you haven’t noticed)
And I feel like he’s the only guy who 1) can adapt to Rory’s needs for the future while 2) still being an anchor to home/the past. I think you see this best in season six when she dropped out of college. Seeing him brings her back down to earth and reminds her again of who she was before, but more importantly, it pushes her to go forward. I feel like Dean was too tied to Stars Hollows “high school” Rory, while Logan never fully understood where she came from, so the balance that Jess has is incredibly delicate and valuable. That comes for a deep understanding/knowledge of who Rory is, which is more than just “oh he likes to read too”. It’s not that he reads books, it’s that he’s able to read her. And the wonderful part is that Rory is able to the same for him.
So one thing I’m excited about in the reboot is to see how the nature of this relationship continues as Rory’s drifting about adulthood. Her mom and family are the most important relationships, without a doubt. But between the three guys, I wouldn’t be surprised if Jess is the one to help pull her out of the funk. That’s just how their relationship works. “It is what it is.”