Model Jenny Shimizu can count two of the most famous women in the world as her former girlfriends, as back in the 90s she dated both Angelina Jolie and Madonna.
Now, the model is opening up about her time dating the "Lucky Star" singer, while she enjoyed her own professional success as an openly gay model working in the fashion industry. Jenny spoke about their relationship in the final installment of the six-episode docuseries In Vogue: The 90s.
"I mean, you’re not gonna say no to Madonna in the '90s," she exclaimed. "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?'"
The former Banana Republic model explained: "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."
Jenny joked: "My wife is going to kill me," as she reflected on the time period, referring to Michelle Harper, whom she tied the knot with in 2014.
Nevertheless, the model appeared to be nostalgic about that time, when she appeared on her first campaign billboard on Times Square.
"That time was so crazy and fun," she said. "There's really something heartfelt about certain moments."
"I remember my friends bought 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 explained wistfully.
"Being Japanese and having my parents going through internment camps, and being gay, and — to walk down the street and always get harassed in some way, for one second, seeing that campaign… it was such a, you know, it was a big statement. And I really am grateful to Calvin because he actually did something that was so positive globally," she continued.
Madonna wasn't the only star who counts Jenny as a former partner; Angelina Jolie had nothing but praise for the model as she opened up about their time together during an interview with Girlfriends Magazine in 1997. The former couple starred in the film Foxfire together.
Angelina reportedly said that Jenny "could have been a deep love" for her, adding: "I probably would have married Jenny Shimizu if I hadn't married my husband."
At the time of speaking, Angelina was married to Jonny Lee Miller, but she said of her relationship with the model: "I fell in love with her the first second I saw her."