Which Other Hollywood Superstar Did Madonna’s Ex Jenny Shimizu Date? Find Out As Model Opens Up About Steamy Romance With Pop Icon

As a fervent admirer of extraordinary lives and their intricate narratives, I find myself captivated by the tale of Jenny Shimzu – a woman who traversed the glamorous worlds of fashion and pop culture, leaving behind a trail of enchanting anecdotes. Her account of dating Madonna in the ’90s, as portrayed in her upcoming docuseries, is a testament to the allure that the Material Girl held then – so potent that it could transform even a professional runway model into a high-class hooker, albeit temporarily.


In an upcoming documentary series, Madonna’s former girlfriend, Jenny Shimzu, has shared insights into their relationship. Interestingly, before fame struck, Jenny also dated Angelina Jolie – a connection established during their romantic past.

During the TV show interview, Shimzu reminisced about her experiences with the musician, having traveled to various European cities together. In an open discussion about her relationship with the pop icon Madonna, the ex-Calvin Klein model disclosed that she often felt like a sophisticated escort.

Regarding her experiences with Madonna during the 90s, Shimzu expressed in the documentary episodes that it wasn’t something one could refuse. She also added, “It felt quite luxurious, in a way, to be compared to a high-class escort – and indeed, it was. You’d receive a call saying, ‘Hey, can you join me at my Paris concert? Aren’t you currently in Europe?’

In simpler terms, the model shared that during her busy schedule, she’d wrap up a fashion show, rush to catch a late-night flight, meet a singer, spend the night together, and then depart early the next morning. She casually mentioned in one of her recent interviews, “I’d say something like, ‘Oh, I’m just wrapping up Prada now. Immediately after that, I’ll hop on a plane.’ And I would indeed. I’d visit her at the Ritz around 4 am, spend time together, and then jet off back to Milan.

Speaking about her experience with the singer known for “Like a Player,” Shimzu explained that neither of them had deep emotional connections; instead, their relationship solely revolved around intimacy.

In a passage from her memoir, the model expressed that the relationship wasn’t about forming an emotional attachment; rather, it was centered around achieving the pinnacles of sexual bliss together. She also mentioned that she found pleasure in being at this woman’s service. The act of being summoned to her room whenever desired for intimacy added to her excitement.

Regarding Jenny’s relationship with Angelina Jolie, it was stated in an interview from 1997 that if Jolie hadn’t met her ex-husband, she might have married model Jenny instead. Interestingly, Jolie confessed that she fell in love with actress Shimzu the instant she laid eyes on her, expressing, “I was smitten the very first second I saw her.

Yet, the affection between them proved fleeting, as Angelina Jolie wed Brad Pitt, and Shimzu married Michelle Harper, in 2014.

In Vogue is now available to stream on Hulu.

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2024-09-24 17:37