Madonna’s Most Surprising Relationship Blows Away Her Sean Penn Affair With Ease: ‘It was great feeling like a high-class hooker’
- Hung Up singer Madonna is a huge supporter of LGBT+ rights and has never put a label on herself.
- Madonna dated model Jenny Shimizu in the 1990s and the former Banana Republic model is now coming clean about it.
- Jenny Shimizu has previously recounted the relationship in her tell-all memoir.
Madonna, often referred to as the Queen of Pop, is also the queen of millions of hearts. Some people have also been lucky enough to have the Hung Up singer’s heart and it is not just men who have had that kind of fortune.
It is no secret that Madonna has always advocated for LGBTQ+ rights so it is not too hard to believe that she has dated a woman at some point in her life. She has never been one to put labels on her s*xuality and recent reports suggest that she was once in a relationship with a female supermodel.
Madonna Dated This Supermodel Back in the 1990s
Madonna began her career as a backup singer and dancer for the French singer Peter Hernandez. Her first record deal was with Gotham Records in 1981. However, that did not last long, and the next year, she was signed to Sire Records. Her first two singles Everybody and Burning Up/Physical Attraction reached number three on Billboard magazine’s Hot Dance Club Songs.
The Material Girl singer quickly rose through the ranks and soon, she was one of the biggest pop stars in the industry. She has also dated her fair share of celebrities including Sean Penn and Tupac Shakur. Although she has never admitted it publicly, she was involved with model Jenny Shimizu for some time in the ’90s according to the Japanese-American model herself.
In the new docuseries In Vogue: The 90s, Shizimu has opened up about the time she had a private relationship with the songstress (via People).
I mean, you’re not gonna say no to Madonna in the ’90s. Not only was it great feeling like a high class hooker — because really it was. You’d get a phone call like, ‘Hey can you meet me at my Paris show. You’re in Europe right?’
So I’d be like, ‘Yeah, I’m just finishing Prada. Right after Prada I’ll catch a plane over.’ And I would. I’d go over to her hotel, to the Ritz, at like 4 in the morning, have s*x, and then fly back to Milan.
The former Calvin Klein and Banana Republic model is now married to Michelle Harper. The couple tied to knot in 2014 and Shizimu joked that her wife would be mad at her for discussing her affair with Madonna.
Madonna Had a Tumultuous Relationship with Sean Penn
Considering the world has witnessed Madonna locking lips with Britney Spears and Christina Aguilera during a performance at the MTV Video Music Awards in 2003, it might not come as much of a surprise that she once had an affair with Shizimu.
That said, the Evita actress was married to Sean Penn in the 1980s. The duo met each other on the set of the singer’s Material Girl music video. What started as a fling soon turned into a full-on romance. They tied the knot just six months later. However, the relationship became rife with issues soon.
Part of the reason for the problems in their marriage was Penn’s insecurity and jealousy when it came to the songstress. In April 1986, the actor attacked songwriter David Wolinski who was speaking to Madonna. According to a source close to People, their relationship hit a new low after this incident.
In June 1987, Penn was sentenced to 60 days of prison for speeding through a red light while being drunk By this time, his reputation had taken several hits due to his temper issues. He was also accused of abusing his wife. However, according to The Daily Beast, she insisted that all those allegations were false. The couple got a divorce in 1989, and just like that, one of Hollywood’s hottest couples no longer existed.
In Vogue: The 90s is available for streaming on Hulu.
