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Vanilla Ice Just Shared New Details About Relationship With Madonna

The Queen of Pop once proposed to the rapper, he claims.

They may seem like an odd couple now, and if you ask Vanilla Ice, dating Madonna seemed just as unlikely to him at the time. The two were together in the early 1990s when Vanilla Ice (real name: Robert Van Winkle) was just coming to fame and Madonna had already spent nearly 10 years as one of the most famous pop stars on the planet. Their romance didn't work out—and her controversial Sex book played a major role in its demise—and in a new interview, Vanilla Ice shared just how intense the relationship got before it ended.

Speaking to the podcast Just Jenny with Jenny Hutt, Vanilla Ice disccused Madonna's proposal to him, how upset he was about her book, and what a whirlwind the whole relationship felt like. Read on to see what the "Ice Ice Baby" rapper had to say about his famous ex.

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He was surprised she was interested in him.

In the interview (warning: explicit language in the video above), Vanilla Ice said that Madonna approached him after one of his shows.

"I remember she came back to the dressing room, said hello to me, and she kind of gave me the sexy eyes and I was like, 'Well, she's really too old for me, so I must be mistaken on that … That couldn't be. That's Madonna,'" he said. At the time, Vanilla Ice was in his early 20s and Madonna was in her early 30s. They were set up on a date, and the relationship took off from there.

He claimed that Madonna proposed to him.

Madonna performing in Los Angeles in 1989
Michael Ochs Archives/Getty Images

"She even proposed to me," Vanilla Ice said on the podcast. "Things were going so crazy and fast, man. I was just like, 'What? I thought the guy was supposed to do that. What do you mean? Wait a minute, this is too fast. I'm just getting started here and I'm way too young for this.'" He added, "The more I think about it, the more crazy it was."

Madonna has never addressed that claim publicly, but this isn't the first time the rapper has recalled the story. "She actually proposed to me," he told Yahoo! in 2021. "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."

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He felt violated by her explicit book.

Madonna at the premiere of "Truth or Dare" in 1991
Vinnie Zuffante/Michael Ochs Archives/Getty Images

In 1992, Madonna released the book Sex, which featured explicit photos of sexual acts. The singer included photos of herself with Vanilla Ice, which he has said he didn't consent to.

"That book came out and I thought it was so [expletive], I didn't want to be a part of it," he said in the new interview. "I said, 'How could you do that to me? And why did you do that to me?' I could've sued her. I didn't want to. I was like, I don't need that controversy. Let's just let it go and you go your way, I go mine."

In a previous interview with News of the World (via Digital Spy) in 2011, Vanilla Ice said that he didn't like what he felt the book implied. "It was disgusting and cheap," he said. "We were in a relationship yet it looked like she was screwing all these other people. I thought she was taking pictures and running round naked because she was like that. Then when the book came out I was so embarrassed and ashamed. It was a porno. She threw me in like I was a product off a shelf and I didn't appreciate it. That was it and I ended it. She said she didn't have sex with these men but it looked like she was."

He doesn't hold a grudge, however.

Vanilla Ice at the premiere of "That's My Boy" in 2012
Kathy Hutchins / Shutterstock

While Vanilla Ice has repeatedly shared his disdain for the Sex book and talked about Madonna's age in interviews, he does have respect for her. "She's great. She's a legend. I think she's one of the greatest ever," the 55-year-old said in the recent podcast. He also said that their relationship was "normal" when you took away the celebrity aspect. "It's just basically her and I, and at that point, it wasn't really anything different than any other normal relationship, really," the rapper explained.

As for Madonna, she hasn't spoken much about Vanilla Ice publicly. In 2015, she told Us Weekly, "[I]f I were trapped on a desert island with either [ex-boyfriend] Vanilla Ice or Dennis Rodman, I would pick Dennis. He has a better sense of humor. Plus, he could always wear my clothes."

She stands by her book.

Madonna at the Cannes Film Festival in 2008
Denis Makarenko / Shutterstock

Vanilla Ice might have a problem with it, but Madonna is still proud of her infamous book. In 2022, she celebrated its 30th anniversary on Instagram (via Billboard), writing, "30 years ago I published a book called S.E.X. In addition to photos of me naked there were photos of Men kissing Men, Woman kissing Woman and Me kissing everyone. I also wrote about my sexual fantasies and shared my point of view about sexuality in an ironic way."

She went on to call out younger celebrities who have been open about their sexuality, including Cardi B, Miley Cyrus, and Kim Kardashian. "You're welcome [expletives]," she added.

Lia Beck
Lia Beck is a writer living in Richmond, Virginia. In addition to Best Life, she has written for Refinery29, Bustle, Hello Giggles, InStyle, and more. Read more
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