'Felt like a high-class hooker..', Madonna's Ex Jenny Shimizu opens up on her relationship with the singer

Jenny Shimizu, the iconic model of the 90s, opens up about her unconventional dating life in the new docuseries In Vogue: The 90s. Embracing her identity as an openly gay woman, Shimizu reflects on her passionate affairs with celebrities like Madonna and Angelina Jolie, offering candid insights into her unforgettable experiences

Amrita Ghosh

First Published Sep 25, 2024, 1:27 PM IST | Last Updated Sep 25, 2024, 1:27 PM IST

Model Jenny Shimizu recently revisited her unique dating experiences from the 1990s, a time when she embraced her identity as an openly gay model while achieving professional success. In her new docuseries, In Vogue: The 90s, the 57-year-old candidly discussed her romantic involvement with Madonna and hinted at her past relationship with Angelina Jolie.

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Shimizu recalled that it was hard to refuse Madonna during that era, describing her experiences as akin to feeling like a high-class escort. She shared anecdotes about receiving spontaneous invitations to Madonna’s events, highlighting a typical scenario where she would finish a Prada commitment, hop on a plane, and meet Madonna at the Ritz in Paris in the early hours of the morning. Shimizu humorously remarked about her life, mentioning that her wife might not be pleased with these revelations.

Nostalgia filled the air as Shimizu reminisced about her first campaign billboard in Times Square. She recalled the excitement of her friends showing her the Banana Republic campaign, which featured the phrase "American Beauty" underneath her image. Shimizu expressed that she had never been described as either American or a beauty before that moment.

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Regarding her relationship with Angelina Jolie, which also blossomed in that vibrant decade, Shimizu reflected on Jolie's past comments. The Maleficent actress had expressed in an interview with Girlfriends Magazine that she might have married Shimizu if her life had taken a different path. At the time, Jolie was married to Jonny Lee Miller, yet she spoke fondly of Shimizu, admitting she fell in love with her at first sight.

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To explore more of Jenny Shimizu’s candid revelations, viewers can catch In Vogue: The 90s streaming on Hulu.