The two actors dated for three and a half years before they broke up in 2006. Whatever is true regarding Bledel and Padalecki, its still has to be exciting for Rory and Dean shippers to know that there is a possibility these two supposedly had a thing off-screen, too.

Did Alexis Bledel and Matt ever date?

By now, most Gilmore Girls fans know Bledel dated Ventimiglia and Padalecki, but the identity of her third on-set romance has remained relatively mysterious. While it would seem natural for Bledel to have also dated Matt Czuchry, that didnt happen.

Why does Dean break up with Rory?

3 Rory And Dean The second time, Dean breaks up with Rory on the dance floor when he gets tired of pretending she and Jess dont have feelings for each other.

Did Rory and Dean ever date in real life?

Gilmore Girls casting director reveals Alexis Bledel and Jared Padalecki secretly dated in real life. During most of the shows seven-year run, Rory and Dean were televisions favorite couple. She revealed to Life & Style Magazine that Alexis Bledel, 35, and Jared Padalecki, 34, actually dated in real life as well.

Are Rory and Jess dating in real life?

RELATED: Gilmore Girls: How Long Was Jess Mariano and Rory Gilmores Relationship? It turns out that Bledel and Ventimiglia didnt need to fake that obvious chemistry between their characters — they were actually dating in real life at the time.

Who does Dean end up with in a year in the life?

Although he never dates Rory again and disappears from the series pretty much entirely after their break-up, Dean briefly appears in Gilmore Girls: A Year in the Life, the 2016 revival of the series. Dean reveals that, since his disappearance, hes married a woman named Jenny and lives in Scranton, Pennsylvania.

Why did Luke not like Dean?

Lukes distaste for Dean in the Bop-it episode stems from the fact that Rory is basically (in Lukes eyes) Lukes daughter and so naturally no guy will ever be good enough which makes matters bad enough to start off with.