Unpopular opinion (maybe): Luke's ultimatum at the end of Season 3 inadvertently reinforced Jess's choices that stopped him from finishing high school in the first place.
Disclaimer: The intent here isn't to attack Luke for how he handled things. The overall effect of Luke's presence in Jess's life is undoubtedly positive and instrumental to where Jess ended up. Luke was put in an unfair position that he wasn't prepared for, he genuinely cared and tried his best with the knowledge he had, and it would have been well within his rights to say no to Liz to begin with or to Jess when he came back after the car accident.
From what Jess tells Rory in "Teach Me Tonight," it sounds like he never had much academic support from adults, which is of course why Rory's belief in him will end up meaning so much. Details about Jess's childhood that are revealed once Liz is around suggest that Jess didn't have trustworthy adults in his life and had to learn how to be self-sufficient early. Even though we as the audience can see that Luke is responsible and trustworthy through his own actions and his relationships with people who have known him for many years, Jess doesn't have the same history with him, and it can take a long, long time to unlearn those survival instincts. Additionally, Jess's Walmart manager, as gregarious and pro-corporate as he seems to be, doesn't appear to engage in the practice of pressuring introverts to socialize (which happened to Rory at Chilton) and allows Jess to do something constructive and work toward a tangible reward. Some people get these benefits from going to school, but Jess didn't. Then there's a layer of youthful hubris here because Jess really did seem to think that he could manage all of this and go to school just enough to graduate based on what he tells Rory in S3 E17, Luke in S3 E18, and the principal in S3 E19. With of all this information in mind, it's really not surprising that Jess would prioritize work above school. His logic is self-destructive but understandable, and his fatal flaw ends up being that he committed to more responsibilities than a person could reasonably handle. This isn't the standard media portrayal of ditching school.
Luke's approach to being Jess's guardian is fairly hands-off. After Luke's "laying down the law" talk in the first episode Jess is in, the only requirement we see enforced is that Jess has to work at the diner, which Jess complies with. Luke didn't know Jess was working at Walmart at all until Jess bought his car, he didn't know Jess was eventually working more than full-time hours, and he didn't know Jess was missing as much school as he was. (This last one suggests a significant oversight at the school, which is another story.) When the extent of Jess's work hours is brought to his attention and Lorelai speculates about what is going on, he tells Lorelai that there is no way Jess would skip school and doesn't investigate further. When he realizes Jess is working some days instead of going to school, he offers to pay Jess more at the diner (and later steals his car) to prevent him from working at Walmart (the place he worked before he had a car to earn the money to buy it???) but doesn't press him about what is really going on.
So after all of that, it turns out Jess didn't go to school enough to graduate. Luke does give Jess the option to stay in Stars Hollow and keep going to school, but I could never blame someone for not being able to have a rational conversation immediately after a stranger randomly shows up, claims paternity, and runs out. The emotional damage of that incident really can't be divorced from what happens here. Luke is of course also in crisis mode. Jess didn't graduate because he worked too much, so now he's in a position where his consequence is to keep doing what got him into trouble, only this time he doesn't have anyone looking after him. This isn't what Luke is intending, but his ultimatum basically reinforces Jess's mindset of prioritizing work (i.e. short-term financial security) above school and his reluctance to trust other people, and it reinforces Jess's family history (ironically not including Luke) of abandoning difficult situations (in this case, the aftermath of the fight with Dean) and relationships (in this case, Rory) instead of facing them. Jess ends up on his own with the money he had from work that he was saving for a different car, so he probably thinks it's a good thing he worked as much as he did, and he ends up without adult guidance or restrictions to help him sort all this out and repair the harm he caused. This could have turned out much more darkly than it did, and it's really a miracle that Jess got to where he was by the time he was 21.
When Jess is with Jimmy in California, he acknowledges that he's failed and doesn't know where to go from there. It probably isn't outlandish to think that Jess was earning more as a full-time forklift driver than what he is earning during Season 4. Factoring in the lower cost of living in Stars Hollow or somewhere nearby compared to New York, he probably could have been able earn a decent living if he stayed at Walmart (even if he wouldn't have been better off in the long run). That's probably why Luke's "I'm sorry I didn't think driving a forklift for the rest of your life was good enough for you" stung. It was likely a much better situation than whatever Jess is in mid-Season 4.
In late Season 4, Jess seems resigned to where he is. He doesn't complain or blame anyone else for his circumstances, even when Luke repeatedly mocks him in New York. (Even mid-Season 4, Jess doesn't express anger toward Luke about anything other than Luke stealing his car until Luke provokes him multiple times.) Maybe Jess was already thinking about writing a book or studying for a GED during Season 4, but his posture and mannerisms seem to suggest defeat more than anything else. At this point, Jess might not be envisioning anything other than what he has. It is only after Luke accepts Jess for who he is, and stops seeing him as a failed project, ("You are who you are. I cannot change that, and I'm going to stop trying.") that Jess really starts to move forward. Although Luke isn't even very positive in how he says this, it's still the sort of affirmation Jess always needed and maybe never received from a family member before. Then, he's honest with Luke about his emotions, he's receptive to Luke's advice, he expresses appreciation for what Luke did for him, he offers Luke a way to stay in contact, and he makes a commitment to pay him back even though Luke says he doesn't have to do so. He tries (and fails, for the time being) to make amends with Rory, and after all of these things happen, he progresses into the version of himself that returns in Season 6. Jess pursues a path that Luke doesn't quite understand but has accepted and is proud of (it's also a path that Rory does understand and is proud of, and both forms of support are so important).
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