Why Madonna's Ex Jenny Shimizu Felt Like “a High Class Hooker” During Romance

Model Jenny Shimizu looks back on her unconventional romance with Madonna in the '90s.

The 57-year-old opened up about her love affair with the “Material Girl” singer in the new Hulu docuseries In Vogue: The 90s.

"I mean, you’re not gonna say no to Madonna in the '90s," she said in the six-part series’ final episode. "Not only was it great feeling like a high-class hooker—because really it was. You’d get a phone call like, ‘Hey can you meet me at my Paris show? You’re in Europe, right?’"

Jenny said she’d respond to Madonna’s request, saying, "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 four in the morning, have sex, and then fly back to Milan.”

Of the '90s, the Calvin Klein and Banana Republic model, who was also romantically linked to actress Angelina Jolie throughout the same time period, said, “That time was so crazy and fun. There’s something heartfelt about certain moments.”

Jenny also opened up about the impact of being featured as model on a giant billboard that read “American Beauty.”

“Being Japanese and having my parents go through the internments camps and being gay, to walk down the street and always get harassed in some way, for one second seeing the campaign and being like, ‘Wow,’” she said. “It was a big statement, and I really am grateful to Calvin because he did something that was so positive globally.”

Madonna, who was previously married to Sean Penn and Guy Ritchie, has long been an icon for the LGBTQ+ community.

Of her sexuality, the pop star told Advocate in 1991, “I think everybody has a bisexual nature. That's my theory.”

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