From Catwalk to Celebrity Affairs: The Intriguing Life of Jenny Shimizu

The Scandalous Life of Jenny Shimizu: The Model Who Captivated Madonna and Angelina Jolie

In a shocking turn of events, the 58-year-old Asian-American trailblazer, Jenny Shimizu, was spotted in West Hollywood, CA on Sunday with her wife, Michelle Harper, ahead of their 11th wedding anniversary. But what's truly fascinating about this stunning model is her checkered past, which has included romances with some of the most powerful women in showbiz – including none other than Madonna and Angelina Jolie.

Shimizu's androgynous beauty first caught our attention back in 1994 when she was scouted outside an LA nightclub to model Calvin Klein's CK One unisex perfume campaign. This led to a modeling career that saw her gracing the runways for top designers like Prada, Banana Republic, Versace, Jean Paul Gaultier, Yohji Yamamoto, Donna Karan, Anna Sui, Thierry Mugler, Levi's, J. Crew, The Gap, L.A. Eyeworks, and the United Colors of Benetton.

But what's truly remarkable about Shimizu is her ability to attract women from all walks of life – including some of Hollywood's most eligible bachelorettes. Her romance with Angelina Jolie was particularly salacious, with Jolie confessing in an interview that she would have probably married Shimizu had it not been for her marriage to Jonny Lee Miller.

"I fell in love with her the first second I saw her," Jolie gushed to Girlfriends in 1997. "I thought she was just reading for my part, but then I realized she was actually auditioning for a different role." Shimizu and Jolie's chemistry on screen was undeniable, particularly in their steamy nude scene together in Annette Haywood-Carter's 1996 adaptation of Joyce Carol Oates' Foxfire.

But what's truly astonishing is that Shimizu had previously dated none other than the Queen of Pop herself – Madonna. In a candid interview with Hulu/Disney+ docuseries In Vogue: The 90s last September, Shimizu revealed the intimate details of her relationship with the singer.

"I mean, you're not going to say no to Madonna in the nineties," Shimizu laughed. "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'd be like, 'Yeah, I'm just finishing Prada, I'll catch a plane over.'"

Shimizu's romantic escapades didn't stop there. The model also had a high-profile affair with actress Ione Skye, which involved strap-ons and safe words. However, the relationship ended abruptly in 1999 when Skye started feeling "needy and devoted."

"[She was a] masterful lover, sometimes a dominant one," Skye wrote in her memoir Say Anything. "But Jenny didn't want me to be her dog. She left shortly thereafter for a modeling job and never came back to me, except as a good friend."

Shimizu's love life has been the subject of much speculation over the years, with some of her most notable relationships including a four-month extramarital affair with Rebecca Loos – the former assistant of David Beckham.

In 2005, Shimizu and Loos even staged a mock wedding ceremony to protest the States' laws on same-sex marriage. The ceremony, which aired as Power Lesbian UK on Logo TV, was a bold move by the couple, who were committed to fighting for equality.

Today, Shimizu is married to Michelle Harper, with whom she shares an unbreakable bond. As they celebrate their 11th wedding anniversary on August 30, we can't help but wonder what's next for this captivating model – will she continue to break barriers and defy expectations, or will she settle down and live happily ever after?

One thing is certain: Jenny Shimizu is a true trailblazer, a woman who has lived life on her own terms and refused to conform to societal norms. Her story is one of courage, resilience, and unwavering commitment to oneself – a truly inspiring tale that will leave you breathless and wanting more.

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