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Milo Ventimiglia was already a heartthrob on Gilmore Girls. The role of Jess began the legacy of heartthrobs like Peter Petrelli and Jack Pearson. One of Jess’s Gilmore Girls love interests was Shane (Jessica Kiper). Kiper recalls Ventimiglia bringing her to a church when they were filming. 

'Gilmore Girls' star Milo Ventimiglia stares into camera
Milo Ventimiglia | Barry King/WireImage via Getty Images

Kiper was a guest on Scott Patterson’s I Am All In podcast on April 15 to discuss her role on Gilmore Girls. Patterson asked for “Milo stories” and she obliged. Boy howdy, did she oblige!

The church near ‘Gilmore Girls’ 

On Gilmore Girls, Jess and Shane make out at the Stars Hollow End of Summer Madness festival. In real life, Ventimiglia was more reserved.  

“One day on set, and I don’t think it was my first day, it could’ve been, it’s all a blur,” Kiper said on I Am All In. “One day, on break, for lunch or something, he went to a Catholic church. He brought me. I don’t know why I went with him or he asked me or how that worked out. But we were hanging out and he was going. So I was with him and we went to this Catholic Church very close to Warner Brothers and he went in and spoke to a priest.”

Jessica Kiper speculates on Milo Ventimiglia’s ‘Gilmore Girls’ confession

Ventimiglia was a single man at this point on Gilmore Girls. It was before he started dating Alexis Bledel. Kiper was married at the time. She’s married now, but to a different husband. She suspects that gave Ventimiglia pause about their kissing scenes. 

“He didn’t try and convert me or anything,” Kiper said. “I’m not Catholic but I don’t know what he went to speak, maybe about something. Maybe he was researching something or maybe he felt bad about kissing a married woman. I have no idea because we went for it. We didn’t fake it.”

Milo Ventimiglia showed even more kindness to Jessica Kiper 

Patterson loves “Milo stories” because they’re always this good. Even before the Catholic church excursion, Ventimiglia made Kiper feel welcome on the Gilmore Girls set. Kiper’s first episode was obviously not very acting or dialogue heavy. Still, Ventimiglia wouldn’t leave her hanging in the guest stars’ trailer.

“My first day, the AC did not work in my crappy little non star trailer,” Kiper said. “I don’t think I even had a TV. So he let me hang out in his trailer which was a Star Wagon that had an AC. So I just watched TV in his nice air conditioned posh wagon while he, very Jess like I guess which is weird because Jess is kind of a jerk. But anyway, he’s sitting outside reading a book on his stoop.”