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Model Jenny Shimizu is looking back on her unconventional dating life in the 90s. At that time, she not only lived her truth as an openly gay model but also enjoyed professional success. In her new docuseries, In Vogue: The 90s, the 57-year-old opened up about her love affair with Madonna, even teasing about the time spent with Angelina Jolie, whom she reportedly dated back in the day.
“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?'” she said in the Hulu series.
Shimizu continued, “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 sex, and then fly back to Milan.” The model went on to joke, saying, “My wife is going to kill me.”
Nevertheless, Jenny Shimizu got nostalgic as she recalled the time when she appeared on her first campaign billboard in Times Square. “That time was so crazy and fun. There’s really something heartfelt about certain moments. I remember my friends brought me to Times Square and said, ‘Look!’ And I had just done a Banana Republic campaign. And underneath it said, ‘American Beauty,’ and never in my life had I been described as American or as a beauty,” she said.
As for speaking about Jenny’s relationship with Angelina Jolie, which also happened around the same time, the Maleficent actress told Girlfriends Magazine in 1997, “I probably would have married Jenny Shimizu if I hadn’t married my husband.” At that time, the actress was already married to Jonny Lee Miller, but speaking of her relationship with the model, she said, “I fell in love with her the second I saw her.”
To catch on Jenny Shimizu’s candid revelations, you can tune in to In Vogue: The 90s on Hulu.
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