Jenny Shimizu Describes Her Relationship with Madonna as a “High-Class Hooker”

As a global cultural icon, Madonna metaphorically moved mountains in the music industry with her ability to effortlessly blend social, sexual, and religious themes into her image and sound. With hits like “Material Girl” and “Like a Virgin” dominating the ’80s, it’s no surprise that everyone was emulating the Queen of Pop or trying to get as close to her as possible. For one bold model and fashion icon, Jenny Shimizu, that actually became a reality.

In Episode 6 of the Hulu docuseries In Vogue: The '90s, Jenny candidly opened up to cameras about her relationship with Madonna, noting that they had a few intimate moments in the '90s, which she described as "so crazy and fun." So, what type of relationship did Jenny and Madonna actually have? Well, it wasn't exactly traditional, but then again, when was Madonna ever described as such? Keep reading for all the juicy details on Madonna and Jenny's dating history!

Madonna was in her prime in the '90s, to say the least, and Jenny was well aware of it. But Jenny was also in the spotlight as an openly gay model scouted by Calvin Klein. She later walked for Prada in 1993. Perhaps that attention is what drew the two together.

In the docuseries, Jenny goes into detail about her time with Madonna, admitting, "not only was it great feeling like a high-class hooker, because it really was. It would be, like, you know, get a phone call, ‘Hey, can you meet me at my Paris show? You're in Europe, right?’"

She continued, “So, I’d be like, ‘Oh yeah, I’m just finishing Prada. Right after Prada I’ll catch a plane over.'” She then explained that she would go to Madonna’s hotel, “I would go to the Ritz at 4 o’clock in the morning, have sex, and then fly back to Milan.”

If Jenny and Madonna's meet-ups sound more like something out of a romance film that hinges on exciting sexual escapades, it’s because that’s sort of how Jenny described them. In her memoir released in 2023, she wrote, "It wasn't about an emotional bond, it was about taking each other to the heights of sexual ecstasy," she wrote (per People). "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."

While it’s unclear how long things lasted between Jenny and Madonna, sources speculate that their romance may have overlapped with the budding relationship between Jenny and Angelina Jolie. In a 1997 interview with Girlfriends magazine, Angelina admitted, “I fell in love with her the first second I saw her." However, things eventually fizzled out between the two, and Jenny is now married.

After spilling the tea about her sexual encounters with Madonna in the Hulu docuseries, Jenny jokingly admitted, “My wife is gonna kill me.” So, you’re probably wondering who the lucky lady is, right? Jenny is married to fashion entrepreneur Michelle Harper. The pair wed in August 2014, and they’ve been together ever since.