I’ve recently finished re-watching every Gilmore Girls episode, and my opinion, which was previously pro-Logan, has changed once more back to pro-Jess. I still like Logan, don’t get me wrong, but the more times I watch it, the more obvious it becomes that Logan is not the great love of Rory’s life - Jess is.
Right from when they meet, Rory and Jess firstly have this incredible chemistry (even before they are officially together - yes they like each other but it’s not admitted at the time - they crave spending time together) - but they also have this way of absolutely completely believing in each other in a way that nobody else does. Rory tells Jess that he could do more with his life, and continues to defend him when Lorelai hits the roof about the car crash; a few seasons later, Jess comes to Rory to show her the book he has written, and says he couldn’t have done it without her. Meanwhile, even when Rory is still with Dean, and even though it is a path that he himself does not want to follow, Jess ardently encourages Rory to persevere with Harvard (“Still doing the Harvard thing?” “Yup!” “Good.”). Once again, a few seasons later, when Rory drops out of Yale, it is Jess who gets her back there.
Jess was being told by the world that he was a waste of space and worth nothing - but Rory believed in him, and so it was that piece of hope he clung to and I honestly believe it was that piece of hope that got him to where he is in Season 6. Rory was being told by the whole world that dropping out of Yale was a terrible idea, but nobody got through to her - however, within literal hours of Jess asking her what the hell she was doing, she was back there.
The two of them also come back for each other in a way that simply doesn’t happen with her others boyfriends, not in the same way anyway. Jess leaves for California, and comes back to tell her he loves her. (Luke reacts by saying, “Rory still?! That’s ancient history!” To onlookers, it might be. But for Jess, really, there only has ever been one person for him.) Later, he comes to Yale to tell her he’s in love with her again, and that they belong together. We then don’t hear from Jess for a while, but when we see him again he is giving the book to Rory; he isn’t resentful that she rejected him. Our final sighting with Jess is then when Rory goes looking for him instead, and you feel an excitement from her about his success. What’s interesting to note is that Jess is the person she cheats on both her other boyfriends with; and by this point, Jess stands up for himself in a way he didn’t when she wouldn’t break up with Dean, saying, “This isn’t fair on me, Rory.” But the resentment still isn’t there. As he puts it, “It is what it is, you and me.”
I am utterly convinced the revival episodes will end up with Rory and Jess becoming canonical. Firstly, Milo is in 3 of the episodes, so we can tell Jess is going to be playing a fairly big part. But secondly - how could they not. Rory and Jess bring out the best in each other; and the last time we saw Jess, he still had the attributes that made him and Rory compatible in the first place, except this time he also had his life together, and was finally in a place where he and Rory would work. I strongly believe that the biggest issue for Rory and Jess wasn’t compatibility - it was timing. And in the revivals, I suspect that timing will finally be in the right place.
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