Ooh, ooh, I saw this the other day and wanted to interject. This makes 150% sense! Because the conflict of Rory's arc is not actually "Stars Hollow vs. Wealthy Ivy League." It's actually "Stars Hollow vs. Wealthy Ivy League vs. Rory." And Jess is not there willy-nilly in the mix, he plays into the triad in a super specific way. Let me explain:
From a narrative perspective, it's no surprise that Jess is introduced in season 2, and not earlier or later in the series--and in the episode directly after Lorelai and Rory take a road trip to Harvard, a place she'd never been despite wanting to go there her whole life. In season 1, Rory's life is split between navigating friendships and relationships in Stars Hollow, and exploring the newfound world offered to her by her grandparents' wealth and Chilton. Her future is still nebulous. Not so in season 2. Rory is now a junior, and those college applications are breathing down her neck. The very first episode sees Dean and Rory fight over her commitment to her extracurricular activities, seemingly over spending time with him. The season makes it clear that Rory's arc now has a third aspect to it: her future as a foreign correspondent.
Thus, enter Jess. As others have pointed out, he doesn't fit in either world, which might aid their connection as Rory feels caught between them, but I'd argue that more importantly, Jess is from the world that Rory so desperately wants to join but is terrified of. Jess, for all intents and purposes, is Rory; they are, essentially, the same character, separated by impact of childhood trauma. But Jess is less inhibited than Rory is. He's more confident, bolder, brasher, and much more sure of himself and his future than she is of her and her future. Even if his future is doing "whatever, wherever" and hers is "Harvard, then foreign corespondent." She needs Jess's confidence, and so he gives it to her: his unabashed faith that she can and will succeed in this new, scary aspect of her life. In return, she lends him her optimism and her wide-eyed idealism he's lost over the years.
Jess leaves, and Rory flounders. I don't think this was 100% an intentional writing choice, since season 4 is clearly supposed to mirror the beginning of season 1 (little fish in a big pond), but it says a lot that when Rory's life narrows to only "Stars Hollow vs. Wealthy Ivy League," she loses something intensely fundamental about herself, and spirals into making poor choices. It requires Jess coming back into her life once again to remind her that there is this other part of her that she forgot exists to put her back on track.
From a narrative perspective it makes sense that Logan and Dean aren't threatened by each other; not only do they represent spheres of her life that are actively being explored (and neatly separate, despite being in conflict with each other), the narrative makes it clear that Rory isn't meant to choose Stars Hollow or Wealthy Ivy League--she's meant to strike out on her own and find her way. This is, after all, the end of her story in the series proper. She's left Dean behind, symbolically leaving Stars Hollow in her childhood. The finale sees her leave Logan behind, symbolically leaving behind the Wealthy Ivy League as she takes a job being a domestic correspondent for the Obama campaign. This was always supposed to be the end of Rory's arc. It's even the end of her arc in the revival, with Rory once again leaving Dean and Logan behind to rediscover the part of herself she'd lost, a part which Jess represents not only as the guy who gave her the blueprints to move forward, but as the only ex she doesn't get closer with.
Dean and Logan are, however, both threatened by Jess. Both for his complete understanding of Rory and their obvious bond, but also because he represents the part of Rory that would take her away from either of them. Dean and Logan, at their core, are not much interested in Rory herself but in how they can "keep" her. Dean is chronically insecure about his place in Rory's life, clingy and jealous 24/7 even when he's having an affair with her. Logan makes decisions about their future together without once consulting her, and gets ticked when she understandably balks. Jess's role in Rory's life, time after time, is to remind her of the part of herself that isn't Stars Hollow or Wealthy Ivy League, and that is a threat to her relationship with both Dean and Logan, at different times. I also think this is the main reason Lorelai dislikes Jess, as Lorelai is very much Team Stars Hollow.
This got long and a little rambly, but I live for this kind of meta analytical opportunity. I hope it's halfway coherent.
vaporwave
kianamaiart
ellievsbear
titsay
origamiaround
