Gilmore Girls: A Year in the Life is bittersweet for Team Jess fans. On the bitter side, Milo Ventimiglia gets precious little screen time — he doesn't even show up until the third episode — and when he finally does appear, it's almost like the writers forgot Rory and Jess were ever a thing. Rory doesn't even hug him when she sees him for the first time in at least four years! By the time Fall came around, I'd given up hope that there would be any hint of romance between Rory and Jess, even though we do learn that Jess is still available, unlike Dean and Logan (not that Logan's engagement stops Rory from going for him, but that's another story).
But like I said, it's bittersweet, and the sweetness comes in that final episode. In the last scene that Jess appears in, he's leaving the Gilmore house and talking to Luke on the porch when Rory excitedly shows Jess the first three chapters she's written for her book. (It's nothing earth-shattering, but at least she actually makes physical contact with him.) But it's what happens next that really counts: Luke asks Jess point blank if he's still into Rory, and while Jess says that's "long over," he then proceeds to look into the window at Rory in a very obvious announcement to the audience that Jess still has feelings for her.
While it may not seem like much, that moment actually speaks volumes. First of all, the writers definitely did not have to end Jess's story that way; they just as easily could have given Jess a serious girlfriend, or simply left Jess and Rory as friends (and um, step-cousins). But the door for that relationship was very intentionally left open, meaning that of all of Rory's love interests, Jess has the best chance of actually ending up with her. Plus, if the series is coming full circle with Rory being pregnant, then Rory becomes the new Lorelai, and Logan is the new Christopher, leaving Jess as the new Luke, and more importantly, the right one for Rory. Kind of poetic, isn't it?