Jess Mariano has always been my least favorite of Rory’s boyfriends. Well, I don’t count that one boyfriend on “A Year in the Life” because I don’t even know what was that about.
See, my problem with Jess is that I never made much sense out of him. Not that much in the early seasons, but later, when he kept reciting how important Rory was to him and his life.
Jess was the troubled, dark, and sad boy who suddenly appeared to dismantle Rory’s relationship with Dean. Maybe that would have been fine, (we’re talking teenagers here after all, and Rory was the one who truly initiated first with the power-kiss move) but he proved to be the worst boyfriend I could ever imagine.
Yes, he never yelled at her like Dean did and they shared a love of literature. On the other hand, he was never confrontational, barely cared about her life and connections in Stars Hollow, and he let her down by leaving without even saying a proper goodbye – just because he wouldn’t have been able to handle it.
Now, I do get two things:
- Jess’s behavior stems mostly from his own immaturity, but also the emotional neglect he’s endured from his parents. At the party, his lack of boundaries painted him in a really bad light.
- He really hyped Rory up when it came to her potential. He believed in her, and I don’t doubt that for a second. He believed she could achieve anything she wanted – especially academically and professionally. He never doubted she’d achieve to enter Harvard or any equal university for that matter.

On my first watch, I didn’t get Jess’s behavior in seasons 5 and 6. How come he said to Rory that he loved her out of the blue – and then bailed again? What was he even thinking when he asked her to leave with him at the end of her first year in Yale? Then, more than a year later he told her that he couldn’t have written his book if it wasn’t for her.
Was he just obsessive at this point like the other character I love to hate, Joe Goldberg from “You”? Why did he just seem unable to move on from a teen romance that didn’t last long, and, after all, he ran away from?
Last night, I watched the epic “Why did you drop out of Yale?!” episode, and something finally hit me.
Jess has romanticized the idea of Rory, and might be in love with just it and not the person Rory is. As I mentioned earlier, Jess was never a good boyfriend for her. That didn’t really stem from a lack of feelings for Rory though, but from his own inability to open up, express his feelings, and actually be there for her. That still didn’t stop him from having high expectations and believing in her. He was certain that Rory would be the perfect student no matter what. All those expectations came -surprisingly- from the teenager who dropped out of high school without any care. In his case, things were simple because he just believed he wasn’t made for it. But Rory was. On top of that, Rory just never really had the space to fail because, for Jess and many others around her, that wasn’t even remotely a possibility.
I feel like Jess had Rory placed on a pedestal since the very beginning. He genuinely admired her. She was opiniated, an avid reader, and he probably thought she was smarter than him. Jess was impressed, and I don’t think that anyone else had impressed him up to that point. Maybe that’s another reason why he never really cared about her relationship with Dean. It was obvious he never even considered him a good match for her and kept mocking Dean for his interests and not reading as much as they did. Maybe nobody was too good for Rory after all – including Dean and Logan, and possibly himself.

Now, in the EPIC episode where Jess acts like the absolute GOAT (pardon my enthusiasm) he gets really upset when he realizes Rory is not holding up to his standards. I mean, his first thought when he sees Rory at her grandparents’ is that she has already graduated – and welp, how possible is that even?!
Then, he’s genuinely taken aback when he finds out how Rory spends (or, according to him, wastes) her days. He doesn’t only ask her why she dropped out of Yale, but he also tells her that this is not her – and well, he knows that because he knows her better than anyone else.
That’s quite the statement considering that technically Jess and Rory only dated for around 8 months, and then they met each other only sparsely.
So, all that only makes sense to me if Jess is actually in love with the idea of Rory and not the woman that Rory is actually becoming at this point. Jess has idealized her, and maybe not only because of how much he admires her, but also because of her falling genuinely for him.
The problem is that in season 6 Rory is not the perfect student who loves reading, carries a book everywhere, and puts her studies above everything else. And she never was just that.
Finally, I feel that Jess never saw her for who she is. He never wanted to see her mischievous side. I’m not talking only about the things he naturally missed like Rory sleeping with married Dean or stealing a boat or constantly partying. I’m also talking about the ones he chose to not see: her flirting with and kissing him despite being in a relationship, her following him for a late-night drive, her taking the bus to New York to see him for just a few hours.
So, the issue here is not bad timing and wrong place – or at least, it’s not only that. The real problem is that Jess fell for the idea of Rory, and Rory has always been just a regular human being and not his perfect literary character fantasy.

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Until next time!
