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When it comes to Madonna‘s romantic life, it’s easy to describe it as never boring. The 66-year-old pop star was unapologetic about her sexuality long before it was accepted by mainstream America. Now, one of the Material Girl’s ex-girlfriends is opening up about their super hot romance in the new docuseries, In Vogue: The 90s.
Jenny Shimizu, a former auto mechanic turned supermodel (the ’90s were wild, y’all), gave some eye-opening insight about their time together. “I mean, you’re not gonna say no to Madonna in the ’90s,” Shimizu said in the final episode of the six-episode series. “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?’ ”
“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,” she added. This isn’t the first time Shimizu has spilled the tea on Madonna. In her 2023 memoir, Shimizu admitted that their European nights were sizzling in the sheets and not really anywhere else.
‘It wasn’t about an emotional bond, it was about taking each other to the heights of sexual ecstasy,” she wrote, via People. “I loved the fact that I was at this woman’s beck and call. It turned me on, being ordered to her room whenever she felt like sex.” What’s wild about this whole tale is that Shimizu was also reportedly romancing Angelina Jolie at the time. Jolie had a “deep love” for the model even though she wound up falling head over heels for her first husband, Jonny Lee Miller.
“I probably would have married Jenny Shimizu if I hadn’t married my husband,” Jolie told Girlfriends magazine in 1997, via InStyle. “I fell in love with her the first second I saw her.” That’s a 1990s love triangle we didn’t see coming! All three of the women have gone their separate ways and Shimizu has been married to Michelle Harper since 2014. “My wife is going to kill me,” Shimizu joked in the Hulu docuseries. Don’t worry, Michelle, Shimizu is doing it for all of us who love gossip history.
Before you go, click here to see everyone Madonna has been linked to:
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