According to the book Madonna: Unstoppable, the pop-rapper – real name Rob Van Winkle – and the Grammy award-winner dated for eight months in the Nineties.
He appeared in photographs for her coffee table book titled Sex, which was released in 1992.
Speaking about his past relationship with Madonna, Van Winkle told Yahoo Entertainment that she had once proposed to him.
“She actually proposed to me,” said Van Winkle. “I was like, ‘I’m too young for that. I’m just getting going here, I’m just revving up – I’m sorry.’
“But she was a sweetheart, and we had such a great time. I think she loved, kinda like me now, being the oldest teenager in town.”
Madonna, 63, is nine years older than Van Winkle, 54.
He continued: “We had fun everywhere we went, and we would go just the two of us. It’s funny because we had disguises, so you’d never know it, but we were in public with everybody.
“We went shopping at the malls, we ate at Chili’s and Waffle House. I had a moustache and this crazy wig and glasses and we would go to the movies and stuff.”
He recalled living with the “Like a Virgin” singer on location in Indiana while she filmed the 1992 film A League of Their Own, in which she starred as Mae Mordabito.
The Independent has reached out to a representative of Madonna’s for comment.
According to Van Winkle, Madonna enjoyed his 1991 film Cool as Ice, starring himself, Kristin Minter and Naomi Campbell.
“She loved it, man,” he said. “She was at my concerts and would come out there and dance.
“She loved hip-hop and all the dancing, because she choreographed a lot of her own stuff, too. She’s just a super entertainer.”
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