Jess Mariano's real-life counterpart Milo Ventimiglia argues that it made sense for the young couple to break up, as they were too young to know what they wanted or needed in the long run.
On Scott Patterson's podcast, "I'm All In," Ventimiglia explained: "I think you're going through a developmental change. You are seeing things in the world that you've never seen before" (via Entertainment Tonight). Perhaps in a different time frame, it might've worked. Whatever they had wasn't substantial enough to last beyond that tricky, complicated life transition.
In the 2016 revival of the show "Gilmore Girls: A Year in the Life," audiences got to see Jess and Rory reunite, and Jess was again a source of encouragement and inspiration. Rory laments to him about her situation — that she's broke, has her belongings in boxes, and can't afford to buy new underwear. After Rory laughs off his offer to buy her underwear, Jess pushes her in the right direction.
"You're a writer," he reminds her. "You should write a book about you and your mom." And then at the end of the revival, fans saw Rory excitedly tell Jess that she'd written three chapters of it.
While Ventimiglia might be right about the unsteadiness of the relationship, he forgets to mention the loving support Jess always supplies regarding Rory.
