Madonna’s Ex Jenny Shimizu Felt Like a ‘High-Class Hooker’ While Dating the Singer in the ’90s

Model Jenny Shimizu got real about her past romance with Madonna.

“I mean, you’re not gonna say no to Madonna in the ’90s,” Shimizu, 57, said in the final episode of the documentary series In Vogue: The 90s, which dropped on Hulu Friday, September 20. “Not only was it great feeling like a high-class hooker — because really it was.”

Shimizu rose to fame in the early ’90s for her modeling career. While working as a mechanic, she was approached to model for Calvin Klein in print ads before moving up to the runway. Shimizu made history as she became the first Asian model to walk for Prada and was the first person of color to open the show.

She claimed that while she and Madonna, 66, were seeing each other, the singer would reach out to her to meet her in fabulous places around the world.

“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,’” she said in the doc. “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.”

Madonna and Shimizu’s romance didn’t last long. During the ’90s, the Grammy winner was also linked to Tupac Shakur, Dennis Rodman, Carlos Leon and ex-husband Guy Ritchie. (Madonna welcomed daughter Lourdes with Leon in 1996 and son Rocco with Ritchie in 2000.)

However, Madonna wasn’t the only famous name Shimizu dated during that time. Shimizu also had a relationship with Angelina Jolie. The pair worked together in the 1996 film Foxfire. The following year, Jolie, 49, confirmed her romance with Shimizu.

“I fell in love with her the first second I saw her,” Jolie reportedly told Girlfriends magazine, per InStyle.

While Jolie had a connection to Shimizu at the time, she also was developing feelings for Jonny Lee Miller, whom she was married to from 1996 to 2000.

“He was around when I was figuring things out about myself, when I was realizing that I was attracted to women also,” Jolie reflected. “When I realized that somebody like Jenny could be a deep love for me, he realized it, and he took it very seriously. If anything, he didn’t treat it just like some sexy thing.”

Long after her relationships with Madonna and Jolie, Shimizu met her current wife, Michelle Harper. The couple tied the knot in 2014 after two years of dating.