How do you feel about Jess's character development? Do you love it, or did it lose its impact because most of it happened offscreen? I know you ship Rogan, but do you feel like Jess's development makes him a better match for Rory than he used to be? (Though she regressed rather than evolve, lol)
Great question! I honestly believe that Jess’s “character development” wasn’t necessarily character development, but closure or resolution to his story arc. After season 3, the character had finished serving the purpose of the GG story (i.e., bad boy who created havoc in SH and Rory’s love life, Luke’s troubled nephew who helped Luke grow as a person, and another wrench derailing LL from getting together). Once Jess destroyed his relationship with Rory, dropped out of school, and Luke threw him out of the house, his GG story ended (it was meant to be continued in the spinoff, but not GG). I feel like everything regarding Jess after season 3 is meant to provide closure to Luke and Rory, not continue to develop him or his story. Rory turned him down not once but twice. Her feelings are clear and explicit. Luke and Jess made peace. Jess found his path in life. Resolution complete on all counts. I mean…Jess doesn’t have a story post season 3…he has 20 minutes of combined screen time between season 4 and AYITL, to help other characters develop, not him. He becomes a pure, pure plot device, not an active character.
That being said, from what we do know of adult Jess, I am very glad that he turned his life around and found his path. Given where he started from, it’s admirable that he had the strength of character and will to become his best self and a productive, positive member of society. In AYITL we are given clues that he’s living the kind of life that he wanted. That’s awesome! And if you ask me about the “look,” I didn’t necessarily interpret it as a look of “to be continued love story with Rory” or “wow I’m really still in love with that girl,” but more of “I’m looking back on what could have been.” My anger about that look is that it can be interpreted as “he’s Rory’s one true love” and “Jess is still hung up on a girl he dated for a couple of months 15 years ago” and that, to me, if a GIANT disservice to Jess. He—like any character—deserves better than that.
With regard to Rory and Jess…I’d say that as adults they are highly compatible people. That probably contributes to Jess’s “look.” He knows he fucked up with her. Their relationship as teens was awful. He treated her awfully. He was a terrible boyfriend on all counts. And with every rewatch I’m more convinced that his relationship with her was meant to be seen by the audience as awful. That doesn’t change the fact that they are compatible and could work romantically. That doesn’t change the fact that he loved her and (possibly) loves her still. And if they met as adults in a different way, they’d make a killer couple. I think adult Jess knows this (as does the audience). But the metaphorical ship has sailed. He got his chance, fucked it up, and it’s gone.
I feel like Rory and Jess as adults could work theoretically or in an alternate universe, but not realistically, given where AYITL left us. Regardless of how compatible they are, or how well they could work as a couple as adults, or how Jess may or may not feel about Rory, they have insurmountable obstacles that would prevent that relationship from ever happening. The number one is that Rory is in love with Logan and having his kid. Rory shows zero romantic interest in Jess in AYITL. Her mind is in London. And if Rory wants Logan and does not want Jess, the debate should end. Her choice has been made. I don’t know how to express this without hurting anyone’s feelings, but if a woman does not want Man X, those who want her to be with Man X (because Man X wants her or because the couple seems like it could work, if only the woman changed her mind) are being incredibly unfair to the woman. It reduces the woman to an object of man’s desire. It’s wish fulfillment for the man and eliminates the woman’s agency and desires. And that makes me incredibly uncomfortable. Beyond that, how would a relationship between Rory and Jess realistically work? She doesn’t see him regularly, she doesn’t confide in him, he has a life where he travels and isn’t attached to anything. They’re barely friends…Suddenly she’ll have Logan’s kid and Jess will drop/ruin/undo everything in his life to a) raise Logan’s kid with Rory and b) convince her to love him while she’s still mooning over Logan? How would Rory explain to her kid that her step-father is also her…uncle-by-marriage (is this correct? the family tree is confusing me)? The logistics of them getting together alone give me a headache.
I guess the only way I can answer your question is 1) from the limited info we have, I believe Jess turned out to be a great guy. 2) I’m perfectly happy with his character development happening off-screen because his story and purpose on the show was over, and GG was intended to focus on the Gimore women, not Jess. and 3) I do believe that Rory and Jess would have made a great couple as adults had they met each other as adults, Rory was not in love with Logan and having his kid, and LL were not together (thereby making Rory and Jess related by marriage).
p.s. Jess (and Milo) deserved better.