A past romantic encounter involving Madonna is once again drawing public interest.Though the pop star’s love life often sparks rumors, it has been some time since one of her same-sex relationships became the center of attention.
In the 1980s, Madonna was frequently seen with comedian Sandra Bernhard, and their friendship raised many eyebrows. The duo famously appeared together on David Letterman’s show, wearing coordinated outfits and playfully suggesting there was more to their connection.
Madonna’s past romance with comedian Sandra Bernhard is back in the spotlight, reigniting interest in her same-sex relationships
Despite public curiosity, the true nature of their relationship was never fully disclosed. Not long after, Madonna and Bernhard drifted apart and have remained estranged for years.
Speculation has lingered that their rift may have been due to Madonna’s alleged romance with Ingrid Casares, who had been Bernhard’s girlfriend at the time. While this was never officially confirmed, Casares was featured in a montage of Madonna’s former partners during the Celebration World Tour. Casares and Madonna remain on good terms, with Casares even guest judging the “Vogue” competition during one of the tour stops in Miami.
Madonna’s more intense affair with model Jenny Shimizu, however, is the focus of renewed attention on TV.
Shimizu, a trailblazing model in the ’90s, gained recognition in Calvin Klein campaigns, including the CK1 unisex fragrance ads. She was also among the few Asian models to grace major fashion runways.
In the Hulu docuseries In Vogue: The ’90s, Shimizu opened up about her secret trysts with Madonna. She described jetting across Europe for late-night meetings with the singer, only to rush back to fulfill her modeling duties, as reported by The Daily Mail.
Reflecting on the experience, Shimizu remarked, “Who could refuse Madonna in the ’90s?” Though she felt excited by the affair, she admitted that it occasionally made her feel like a “high-class hooker,” a role she embraced nonetheless.
She recounted receiving calls from Madonna, who would ask her to meet in Paris after a fashion show. Without hesitation, Shimizu would book a flight, heading straight to the singer’s hotel for a late-night encounter before flying back to Milan for her next job.
Shimizu’s connection to Madonna is not a new revelation. The Daily Mail referred to a memoir Shimizu reportedly authored in 2023, in which she shared further details about their sexual escapades. She characterized their bond as purely physical, driven by a desire to explore their sexual boundaries rather than form an emotional attachment.
At the same time, Shimizu was also romantically involved with actress Angelina Jolie. The two had met while filming the 1996 movie Foxfire, and Jolie later revealed in Girlfriends magazine that she instantly fell for Shimizu.
While Shimizu once navigated high-profile relationships with iconic figures, she has since found long-term happiness. She has been married to fashion consultant Michelle Harper since 2014, marking a new chapter in her life.
