Madonna’s past relationships, particularly with Sandra Bernhard and Jenny Shimizu, are gaining renewed attention, especially following revelations in the documentary series ‘In Vogue: The ’90s’.
In the 1980s, Madonna cultivated a close friendship with comedian Sandra Bernhard, with the duo making headlines during a notorious 1988 appearance on David Letterman’s show. Wearing matching outfits, their banter suggested a deeper connection, which led to widespread speculation. However, their relationship had a bitter end, reportedly due to Madonna’s subsequent involvement with Ingrid Casares, who had been dating Bernhard. These events have persisted in public memory due to the entanglements of these high-profile figures.
Casares, a prominent Miami socialite and nightlife impresario, was featured in a montage of Madonna’s former lovers during her latest “Celebration World Tour”, suggesting their past romantic involvement. Casares remains a significant presence in Madonna’s life, even appearing as a guest judge in the Vogue segment of the Miami leg of the tour, held on April 6, 2024.
However, it’s Madonna’s 1990s affair with lesbian model Jenny Shimizu that is capturing attention anew. Shimizu, a breakthrough Asian model famous for her work with Calvin Klein, has shared intimate details of her relationship with the pop icon in the new Hulu documentary series, In Vogue: The ’90s. This series examines pivotal fashion and pop culture moments as chronicled by Vogue magazine throughout the decade.
In the documentary, Shimizu recounts her whirlwind experiences of jet-setting across Europe to meet Madonna for clandestine meetings, balancing these late-night encounters with her commitments to the fashion world. According to Shimizu, the allure of being at the beck and call of one of the world’s most famous women was thrilling, albeit leaving her with conflicted feelings.
“Not only was it great feeling like a high-class hooker, because it was, I would get a phone call saying, ‘can you meet me at my show in Paris, you’re in Europe, right?’ and I would be like, ‘yeah I’m just finishing Prada, I’ll catch a plane over,’” she said. The 57-year-old model continued, “And I would go to the Ritz at four in the morning and have sex and fly back to Milan.”
Shimizu also revealed that her encounters with Madonna coincided with her relationship with actress Angelina Jolie. The two began dating after co-starring in the 1996 film Foxfire, with Jolie expressing her immediate attraction to Shimizu in an interview with Girlfriends magazine. Despite the intense media scrutiny surrounding her past relationships, Shimizu has maintained a stable personal life, being married to brand consultant and fashionista Michelle Harper since 2014.
The resurgence of interest in Madonna’s relationships has inevitably tied back to Shimizu’s continued influence in fashion and LGBTQ+ communities.
In Vogue: The ’90s first three episodes are currently streaming on Hulu and Disney+, with the remaining ones set to release on September 20, 2024.
Source: Noah Wire Services
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