On the show, Dean and Rory date for two years before breaking up because Rory likes Jess. According to what Mara Casey, the casting director for Gilmore Girls told Life and Style in 2016, Padalecki and Bledel did indeed date. “We did have a joke about casting all of Alexis [real-life] boyfriends,” Casey said.

Who did Rory date in real life?

Alexis Bledel as Rory Gilmore Her relationship with Milo Ventimiglia, who played her bad-boy love interest Jess Mariano, was well-publicized. They secretly dated for four years and even spoke of marriage, but their love didnt last.

Did Rory sleep with Dean?

4 Season 4: Rory Loses Her Virginity To Dean Rory has sex for the first time with Dean in the season 4 episode Raincoats and Recipes. This definitely changes their relationship as after being exes for a while, theyre now in a strange place where they realize they still share an attraction and real feelings.