Milo, who played bad boy Jess on the show, joined his on-screen uncle Scott Patterson (aka Luke) for an episode of his podcast I Am All In, during which he explained why he thinks Jess was a great match for girlfriend Rory (Alexis Bledel)... at the time.
Scott read a fan question, asking, "Looking back, what do you think about Jess and Rory's relationship?"
Milo responded, "I think things are complicated when you're young... 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."
So, he said, "I think Jess and Rory, they were what they needed at the moment from each other."
Yet, he acknowledged that the bookworms didn't last on a romantic level. "At the same time, it didn't work out. They went in different directions and that's OK, too. That's kind of great," Milo shared.
"What I did always appreciate about the two of them was—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 continued, noting that there will always be an "outside influence" for young people that suggests how they should behave, what they should read and what they should do.
"But, really, that's just people giving you their version of what they think your life should be," he said. "So, I think Jess and Rory really found their own world and created their own world."
He noted that this kind of bond might be the reason their relationship "lasted beyond just them romantically as teenagers, to where they had an actual friendship as they became young adults."
The This is Us star, now 44, also answered the burning question of whether or not he would come back if the Gilmore Girls team decided to film another revival.
"I can't ever get away from it," he remarked.
However, he said knowing that castmates Scott, Alexis, Lauren Graham "and probably just about everybody else in the show" would agree to do a revival, "it's like, yeah, why wouldn't I?" He added that producers Dan Palladino and Amy Sherman-Palladino would probably be there "writing their asses off" as well.
"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," Milo said.
But he elaborated on why remakes and revivals should only be done for the "right reason," to borrow lingo from The Bachelor.
As he put it, "If it would feel like it was there for the right reason versus the wrong reason—we all know those wrong reasons, where shows think that the show is bigger than the characters, so they'll try to bring it back just to get more money—it's like, yeah, but are there really more stories to tell? That's where I always go back to... Are there still more stories to tell? Have these characters grown to a point where we actually want to see more of them?"
If the answer is yes, he just might be in for another Year in the Life.