Madonna’s ex-girlfriend Jenny Shimizu has joked that she felt like “a high-class prostitute” during the height of their passionate romance.
The 57-year-old model has offered a rare insight into her relationship with the 66-year-old singer in the Disney+ documentary In Vogue: The 90s, which looks back at the stars who defined an iconic decade in the magazine’s history.
In the sixth and final episode of the series, Jenny shared that he enjoyed a romance with Madonna at the same time as he was dating Angelina Jolie, admitting to flying all over Europe to have one-night stands with the star.
The actress, who married wife Michelle Harper in 2014, added that she once flew from Milan to Paris to spend the night with Madonna, before returning to Italy for her next show.
She said, ‘I mean, you’re not going to say no to Madonna in the ’90s.
Madonna’s ex-girlfriend Jenny Shimizu joked that she felt like “a high-class prostitute” during the height of their passionate romance (pictured in 1993)
The model has offered a rare glimpse into her relationship with the singer (pictured) in the Disney+ documentary In Vogue: The 90s
‘Not only was it great to feel like a high-class hooker, because I was, I’d get a phone call saying, ‘can you meet me at my show in Paris, you’re in Europe right?’ and I’d say, ‘yeah, I’m finishing Prada, I’ll be hopping on a plane.’
‘And I would go to the Ritz at four in the morning and have sex and fly back to Milan.’
Jenny, who married wife Michelle Harper in 2014, previously detailed her romance with Madonna in her 2023 memoir, writing that their relationship was driven by a physical connection deeper than physicality.
At the time, he said: “It wasn’t about an emotional bond, it was about taking each other to the heights of sexual ecstasy. I loved the fact that I was at this woman’s disposal. It turned me on to be ordered to her room whenever she felt like having sex.”
The fashion star rose to fame after being offered a job modelling for Calvin Klein and, in addition to being the first Asian model to walk the runway for Prada, she was also the first minority model to open the show.
At the same time that she and Madonna were dating, Jenny was also involved in a romance with her Foxfire co-star Angelina Jolie.
Angelina confirmed their romance herself in a 1997 interview, saying: “I fell in love with her the first second I saw her. I probably would have married Jenny if I hadn’t married my husband (Jonny Lee Miller).”
In the documentary, Jenny also reflected on her own rise to fame as a fashion star, saying: ‘My wife is going to kill me, but that time was so crazy and fun and there was something emotional about it at certain moments.
Jenny shared that he enjoyed a romance with Madonna at the same time as he was dating Angelina Jolie, admitting to flying all over Europe to have one-night stands with the star.
The actress added that she once flew from Milan to Paris to spend the night with Madonna, before returning to Italy for her next show (pictured, 1994).
Jenny married her wife Michelle Harper in 2014 (pictured in 2015)
‘I remember my friends took me to Times Square and they were like, ‘Look!’ And I had just done a Banana Republic campaign and underneath it said American Beauty.
“I’ve never been described as American and as a beauty in my life. Being Japanese and being gay and walking down the street and being harassed, but for a second seeing that campaign was a very big statement and I’m grateful to Calvin Klein because they did something that was very positive.”
The documentary In Vogue: The 90s is a star-studded look at the fashion industry during that decade.
She speaks to former Vogue editors including Edward Enninful and celebrities including supermodel Naomi Campbell, actress Gwyneth Paltrow and Sex And The City star Sarah Jessica Parker.
The documentary also showcases rare and never-before-seen archives from key industry figures and reveals the untold story of the decade’s most celebrated pop cultural moments and movements.
Other contributors will include designers Tom Ford, Marc Jacobs and Jean Paul Gaultier, actress Claire Danes, models Amber Valetta and Tyson Beckford, director Baz Luhrmann and politician Hillary Clinton.
Meanwhile, adding to her long list of romances, Madonna is currently dating Jamaican footballer Akeem Morris, 28.
The couple apparently first met in 2022 after appearing on the cover of Paper magazine’s August 2022 issue.
The final three episodes of In Vogue: The 90s will be available to stream on Disney+ beginning Friday, September 20.
