Just like Rory and Jess on Gilmore Girls, the actors who played them, Alexis Bledel and Milo, were an item in real life. They lasted for more than three years, with the actress telling People in September 2006 about the prospect of tying the knot with her co-star, “I think everybody who has been dating for more than a couple of years probably talks about it at some point. It’s a fun thing for us to talk about, but that’s it.”

Sadly for many fans, Alexis and Milo didn’t make it to the altar, and instead, broke up that same year. In an art imitating real life moment, the actor said on the I’m All In podcast in 2021, “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."