'Gilmore Girls': Milo Ventimiglia Likes That Rory & Jess Weren't Endgame

The original Gilmore Girls ended nearly 15 years ago, but the show’s biggest debate rages on to this day: who should Rory Gilmore (Alexis Bledel) have ended up with? The series sees Bledel’s character cycling through multiple love interests over its seven-season run. Fans still can’t decide if she should have ended up with Dean (Jared Padalecki), Jess (Milo Ventimiglia), or Logan (Matt Czuchry). And Milo Ventimiglia has his own answer to that question. As it turns out, the Gilmore Girls alum is actually glad Jess and Rory weren’t endgame.

Jess and Rory’s timing was never right on ‘Gilmore Girls’

Jess moves to Stars Hollow in Gilmore Girls Season 2, and he and Rory quickly go from verbal sparring to outright flirting. Their chemistry is noticeable to everyone, including Rory’s current boyfriend, Dean. In fact, he eventually dumps her, rightfully declaring that she’s more interested in Jess than him.

Even when they’re free to date, though, Rory and Jess never seem to have the right timing for one another. As Rory is applying to college and making plans to go to Harvard (and later Yale), Jess realizes he won’t graduate high school. The revelation drives him out of town, and the few times he does show up again do nothing to further his and Rory’s feelings for one another.

The two eventually develop a friendship, reconnecting in Gilmore Girls Season 6 and again in Gilmore Girls: A Year in the Life. They still seem to care for one another, but they’re never in the same headspace to rekindle their romance. That’s precisely why Ventimiglia appreciates how things worked out.

Milo Ventimiglia thinks it’s ‘great’ his character didn’t end up with Rory

Ventimiglia recently shared his thoughts on Rory and Jess’ relationship during an appearance on Scott Patterson’s I Am All In podcast. The actor noted how young both characters were when they started dating, and even as the show progressed beyond their relationship. Because they were still growing, he thought their split felt relatable:

“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 like from the heart, from the gut, from the head that you’re experiencing for the first time.”

He also believes that part of what made their relationship so compelling was that they showed up in each other’s lives when they needed one another. In that sense, it didn’t matter if they were endgame. Their relationship still had a massive impact on both of them.

“I think they were what they needed at the moment from each other,” Ventimiglia said. “At the same time, it didn’t work out. They went in different directions, and that’s okay, too. That’s kind of great.”

Could ‘Gilmore Girls’ have continued Jess and Rory’s story?

As for whether or not Jess and Rory could have got the timing right later on, many Gilmore Girls fans think it was a possibility. If the Netflix revival had returned for a second outing, Rory very well could have found her way back to Jess. Of course, it’s just as likely she would have chased after Logan.

Scott Patterson, who plays Luke on the show, saw Jess and Rory’s dynamic as a mirror to his and Lorelai’s. While he believes Rory’s baby is probably Logan’s, he feels Jess would have fought for her in the end. He told Entertainment Weekly as much during a 2016 interview:

“Let’s think of it in terms of who is Amy going to set up to fight for Rory’s affection. Will it be she’s carrying Logan’s child and Jess is going to fight for her because Logan’s going to be schmucky, or is Logan, the rich guy, going to fight for her and Jess is going to be schmucky? I don’t know. I’m thinking it’s Logan’s kid and Jess is going to fight for her.”

Sadly, with no signs of Gilmore Girls making another comeback, fans will be left guessing about Rory’s love life. Ventimiglia is right about one thing, though: her ending up on her own feels like a realistic outcome — especially since she was still figuring things out.

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