Jess is the best boyfriend for Rory. Now there are those of you who will argue other view points. Which is fine, so long as you know just exactly how wrong you are.
Some of those in the audience will argue quite in favor of Dean. A dullard coasting by on looks, who is but a gilded sheen of “niceness”. He is a small-minded and selfish boor, whose niceness is only in evidence when Rory fits the perfect little dollhouse vision of what he wants as a girlfriend. And the moment she has independent thought, independent goals, he flares with anger. He is a cheating ball of slime, who knows he isn’t good enough for Rory and lashes out in violence when he doesn’t get exactly what he wants, when she doesn’t make herself smaller for him.
But there’s a deeper story sense at play as well. Dean is the tempting threat of the future that Rory could have fallen into when her mother turned her back on all opportunity to raise her in the shed behind an inn. He’s the easy way out. The way of not challenging yourself, giving up on ambition, and just getting the shit job that pays the rent now so you can shut off your brain and watch television all night, instead of fighting for a real future for yourself. Rory is smart, yes, but smarts don’t get you a future. Grit and determination do.
Logan is the opposite, heir to fortune, that pissant smug smile of privilege glaring everywhere. He’s the temptation of the other easy way out. Of embracing her family’s money, of coasting on the connections and culture of accomplishment without actually having to achieve it. He’s the one who gets jobs because of his dad, thinks nothing of dropping tens of thousands of dollars on a whim, and has no ambition other than fratbrothing his way to the next honor awarded him on a silver platter.
Jess is the third way, the hard way, the real way. He is the only one of the three who challenges her. And love, the sort of love that shakes the ages, isn’t an easy thing. It’s two storms crashing into each other on the horizon at night. He is not a good person when Rory meets him, but then who of us really is when we are angry and seventeen?
I have been Jess before. I have been the furious teenager who is too smart for the spiteful little schools that close in tightly like a vice around a throat. There but for the grace of a great high school, I would have gone as well.
Dean and Logan use Rory, whether intentionally or not, to make themselves better. In some vain hope that her goodness wears off on them. With Dean she becomes smaller and sadder, with Logan, insufferable and entitled. They feed off of her to make themselves better. Jess, for all his cruelties, and for all the ways he hurts her, makes her better at the same time. And she makes him better.