Milo Ventimiglia Has Made Peace With Jess and Rory Not Working Out on ‘Gilmore Girls’

"They went in different directions, and that's okay too."

Even if you were Team Dean when watching Gilmore Girls, it’s impossible not to feel something for the love story between Rory (Alexis Bledel) and Jess (Milo Ventimiglia). Their story was an emotional rollercoaster ride and Ventimiglia finally shared his thoughts on how the onscreen relationship ended—over 14 years after the series’ final episode aired.

During an appearance on the podcast I Am All In—hosted by Gilmore Girls costar Scott Patterson (aka Luke)—Ventimiglia revisited his character’s love story. “It’s been a while since I’ve thought about Jess and Rory’s relationship,” he said. “I know people always ask me questions about it, but I think, you know, things are complicated when you’re young. I think we can all understand this, I think we can all appreciate it. You’re going through developmental change. You are seeing things in the world 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.”

He then spoke about the characters more specifically. “Jess and Rory, I think they were what they needed at the moment from each other,” he said. “At the same time, you know, it didn’t work out. They went in different directions, and that’s okay too. That’s kind of great.”

Ventimiglia went on to explain how he respected the way in which Rory and Jess made their own world, and didn’t define their relationship by others’ expectations for them.

“I think that’s pretty cool,” he said. “There’s always going to be outside influence to tell you how to behave, what to do, what to look for, what are the pitfalls, what are the glories—’Hey, this what I did when I was your age!’ But really, that’s just people giving you their version of what they think your life should be.”

He continued, adding, “So I think Jess and Rory really kind of found their own world and created their own world, and it lasted just beyond them romantically as teenagers to where they had an actual friendship as they became young adults.”

With how fondly Ventimiglia talks about the Gilmore Girls characters, it’s no surprise that he hasn’t entirely closed off that chapter of his life. He reprised his role of Jess for the 2016 Netflix miniseries Gilmore Girls: A Year in the Lifeand when Patterson asked him if he’d be interested in doing more revivals in the future, he seemed pretty open to the idea.

“The thing is this, I can’t ever get away from it,” Ventimiglia said, responding to Patterson. “For me, knowing that, like, you, Lauren [Graham], 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 asses off, it’s like, yeah, why wouldn’t I?”

However, Ventimiglia said he wouldn’t sign on for more Gilmore Girls unless he felt confident there was more story to tell.

“Have these characters grown to a point where we actually really want to see more of them?” he said. “You want to understand where they’ve been. We’re going to discover something new. So I think if they did want to bring it back, and if it was Amy and Dan at the helm, and you guys were all showing up, I’d be a jerk not to show up.”

Ventimiglia expressed a similar sentiment in a 2017 interview, saying that he would say yes to anything that the show’s creators were behind—but he also got a bit testy, saying that fans should stop asking for more.

“I do kind of feel like audiences shouldn’t get so greedy. They were given a last serving of pie—why don’t we just leave it at that?”

So, for those of us hoping for more time in Stars Hollow, it might be time to move on. However, if you want to marathon watch the series again and take this quiz to find out what Gilmore Girls character you are instead, we certainly don’t blame you.

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