One of Madonna’s same-sex dalliances is coming back under the microscope again.
While the Queen of Pop’s romantic entanglements are routinely the subject of gossip and interest, it’s been a minute since one of her sapphic interludes made headlines.
In the ’80s, Madonna enjoyed a close friendship with comedian Sandra Bernhard. The pair infamously teased their bond during an appearance on David Letterman wearing similar outfits.
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The extent of their relationship has never been fully divulged since Madonna and Bernhard soon had a falling out and haven’t spoken to each other in decades.
Rumors have always suggested the rift may have been caused by Madonna allegedly starting a fling with Ingrid Casares, who had been Bernhard’s girlfriend.
It’s all hearsay, but Casares’ image did appear in a montage of former lovers during Madonna’s Celebration World Tour, one of the first public confirmations of their romance. Casares also remains good friends with Madonna and was a “Vogue” guest judge during one of the Miami stops on the tour.
But it’s Madonna torrid affair with lesbian model Jenny Shimizu that is now burning up TV screens.
In the ’90s, Shimizu appeared in various Calvin Klein campaigns, including the brand’s “unisex” CK1 fragrance ads, and broke ground as one of few Asian models to walk in runway shows for the major fashion houses.
Shimizu has now opened up about her international romps with the “Like a Virgin” singer for the Hulu documentary series In Vogue: The 90s, which looks back at key fashion and pop culture moments in Vogue magazine throughout the decade.
In one the episodes in the series, Shimizu described jetting around Europe to hook up with Madonna for late-night trysts and then having to fly back in the morning to walk in a runway show, according to the Daily Mail.
Shimizu shared: “I mean you are not going to say no to Madonna in the ’90s.” Or ever!
Although she felt a rush getting down and dirty with the biggest pop star in the world, catering to Madonna’s whims also left her feeling like a “hooker,” not that she’s complaining.
“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,'” the 57-year-old added.
“And I would go to the Ritz at four in the morning and have sex and fly back to Milan.”
Sounds like an awesome gig, if you can get it!
This isn’t the first time Shimizu has commented on her time in Madonna’s orbit. The Daily Mail makes reference to a memoir the former model wrote in 2023 (although Queerty has been unable to find any info on the book) in which she went into more detail about her sex-charged affair with Madonna.
“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 beck and call. It turned me on, being ordered to her room whenever she felt like sex,” she allegedly wrote in the book.
Interestingly, Shimizu claims her Madonna rendezvous took place at the same time she was dating Angelina Jolie. We stan a lesbian legend!
The pair began their relationship after appearing in the 1996 film Foxfire together with Jolie later telling Girlfriends magazine that she “fell in love with her the first second I saw her.”
Despite her simultaneous high-profile relationships with A-list icons, Shimizu has been happily married for over a decade.
Since 2014, she’s been wed to brand consultant and fashionista Michelle Harper.
The first three episodes of In Vogue: The ’90s are currently available to stream on Hulu and Disney+. The final three (including the sixth featuring Shimizu’s Madonna tea) will drop on Friday, September 20th.
