Jenny Shimizu Reflects on Her Relationship With Madonna, Says She Felt 'Like a High-Class Hooker'

Former model Jenny Shimizu has opened up about her romantic fling with Madonna during the '90s, which she said felt like being "a high-class hooker."

In an episode of the Disney+ docuseries In Vogue: The 90s, Shimizu spoke about some of the fun she got up to with Madonna in Europe. "I mean, you're not gonna say no to Madonna in the '90s," she said, per People. "Not only was it great feeling like a high-class hooker—because really it was."

Shimizu, who also briefly dated Angelina Jolie in the '90s, said that she'd often get last-minute calls from the popstar asking if she could come see her.

"You’d get a phone call like, ‘Hey can you meet me at my Paris show. You’re in Europe right?’" she said. "So I’d be like, ‘Yeah, I’m just finishing Prada. Right after Prada I’ll catch a plane over.’ And I would. I’d go over to her hotel, to the Ritz, at like 4 in the morning, have sex, and then fly back to Milan."

Now married to Michelle Harper, whom she met in 2012 and married in 2014, Shimizu joked, "My wife is going to kill me."

This isn't the first time she spoke about her relationship with Madonna, though, as she previously shared some details about their time together in her 2023 memoir. She wrote that it wasn't an "emotional bond," but instead "taking each other to the heights of sexual ecstasy." What really worked for her, however, was that she was at Madonna's "beck and call." She added, "It turned me on, being ordered to her room whenever she felt like sex."

As for her relationship with Jolie, which allegedly overlapped with her Madonna fling, she co-starred with the actor in the 1996 movie Foxfire. In an interview with Girlfriends magazine in 1997, Jolie said she and Shimizu kissed after two weeks of filming on the project. She said she "probably would have married" her if she didn't marry her first husband, Jonny Lee Miller.