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Which 'Gilmore Girls' Cast Members Did Alexis Bledel Date?

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Gilmore Girls fans get very passionate about their favorite of Rory's boyfriends (and real talk: are you Team Dean, Team Jess, or Team Logan?) — but did you know actress Alexis Bledel actually dated some of the cast in real life too? I can't blame her...if I was on the show I'd definitely want to date Milo Ventimiglia.
So, which Gilmore Girls cast members did Alexis Bledel date? Let's get into it.
Did Alexis Bledel and Jared Padalecki ever date in real life?

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The romance between Dean and Rory translated into the actors' real lives because Jared Padelecki and Alexis Bledel did actually go out IRL.
The Supernatural star confirmed the past relationship happened during season 1 of Gilmore Girls. “When Alexis and I met, we were both 17 years old and were both Texans and kind of in this new, strange city and I was like, 'Hey, want to go out to dinner?'" he told Glamour in 2021. “I don’t know if we tried to keep it a secret. I wish it was scandalous or something! I think it was more kind of silly.”
How old were Alexis and Milo when they dated?

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Team Jess is always a good place to be ;). I'm convinced these two are endgame...even if Alexis Bledel and Milo Ventimiglia weren't. The actors dated for three years behind the scenes (halfway through filming season 2 around 2002 through 2006).
Milo was around 25 years old when they started dating, and Alexis was around 21.
And there's one more 'Gilmore Girls' star Alexis Bledel dated: Chris Heuisler.
Okay, Chris Heuisler had a small role on the Gilmore Girls, but he definitely made an impression. He was a Stars Hollow High basketball player in Season 2 Episode 11 ("Secrets and Loans"), and even though the character never interacted with Rory, casting director Mara Casey told Life & Style that the actors were briefly together offscreen.
Who's your favorite couple on Gilmore Girls? Even though everyone loves the Rory love rectangle, I really do love Luke and Lorelai — and Emily and Richard!



















