Milo Ventimiglia Reflects on Jess and Rory's 'Gilmore Girls' Romance

Years before Milo Ventimiglia went on to gain Emmy recognition for his role on ABC's This is Us, Gilmore Girls fans knew him for his role as Jess, the knowledgable bad boy and Rory's (Alexis Bledel) love interest. Ventimiglia looked back on two's on-screen relationship in his latest appearance on his former Gilmore Girls' co-star Scott Patterson's, podcast, I'm All In

"I think things are complicated when you're young," the actor said of the two characters, per Entertainment Tonight. "I think you're going through a developmental change. You are seeing things in the world that you've never seen before. You're experiencing things from the heart, from the gut, from the head, that you're experiencing for the first time. So I think Jess and Rory, I think they were what they needed from the moment, from each other and at the same time, it didn't work out. They went in different directions. And that's OK too. That's kind of great."

Jess and Rory carried on a brief relationship in high school, eventually splitting up right before their graduation. The two later reunited as friends in the show's recent limited series update Gilmore Girls; A Year in the Life. Ventimiglia and Bledel also shared a real-life romance, though it was a brief period. "Outside of what anybody wanted to put onto those two, they kind of made their own world and I think that's pretty cool," he said of the fictional couple. 

He also told Patterson that he actually didn't completely relate to Jess's character when he first took on the role. "You and I were always really cool and engaged and had a lot to talk about, but of course, we're playing these characters. Jess was a punk kid who didn't want to hear it from anybody, and Luke was losing his mind with this kid that he got saddled with from his sister," Ventimiglia told Patterson. "You and I could not have been more opposite than who Jess and Luke were. But also where Jess and Luke kind of got to, I think ultimately, was closer to who you and I were in terms of relationship and what not, because I think Jess grew up, Jess learned some lessons and Luke went through some stuff. It's all fascinating."

As for if he would join the cast again for another update, Ventimiglia joked "I can't ever get away from it." 

"For me, knowing that you and Lauren [Graham] and Alexis and probably just about everybody else in the show would show up and on top of it, it'd probably be Dan [Palladino] and Amy [Sherman-Palladino] there writing their a**es off, it's like, yeah why wouldn't I?" he said. "It would feel like it was there for the right reason versus the wrong reason."