There are certain great debates that TV fans will argue about until the end of time, and at the top of that list is definitely the question of who was Rory Gilmore’s best boyfriend on Gilmore Girls. The younger of the two Gilmore girls, played by Alexis Bledel, had three major relationships over the course of the series’ seven-season run: Dean Forester (Jared Padalecki), Logan Huntzberger (Matt Czuchry), and Jess Mariano (Milo Ventimiglia). Now, almost 15 years after the series ended its original run, one of those boyfriends offered his opinion. However, Milo Ventimiglia’s feelings about Jess and Rory’s Gilmore Girls breakup may not make every fan very happy.
Ventimiglia took a break from filming This Is Us to get nostalgic with his former Gilmore Girls co-star (and TV uncle) Scott Patterson on Patterson’s podcast I Am All In. Ventimiglia reminisced about Rory and Jess, who dated in high school but had a rocky breakup and split before they went to college. Although there’s a sizable contingent of fans who will forever root for Rory and Jess, from Ventimiglia’s perspective, things worked out exactly as they should. He told Patterson:
I think things are complicated when you're young. 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.
Before all the Rory/Jess shippers start coming for Ventimiglia, he did also acknowledge that even though he thinks Rory and Jess weren’t Rory and Jess weren’t built to last, he does think they had a really special relationship. He said:
I think what I did always appreciate about the two of them was they — outside of what anybody wanted to put onto those two — they kind of made their own world. And I think that's pretty cool. 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. 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.
Ventimiglia appeared in Netflix’s Gilmore Girls reboot Gilmore Girls: A Year in the Life in 2016, and he’s open to reuniting with the cast for another installment. He told Patterson, “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*sses off, it's like, yeah why wouldn't I?"
No additional reboots of Gilmore Girls have been announced yet, but perhaps if there is one, then Ventimiglia could be open to Rory and Jess rekindling their love. Hey, fans can hope, right?