During an appearance on Just Jenny with Jenny Hutt podcast, the 55-year-old "Ice Ice Baby" rapper opened up about their whirlwind relationship in the '90s, which included her proposing to him pretty early on.
"I was just like, 'What?! I thought the guy was supposed to [get down on one knee],'" he said as he retold the chain of events. "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!"
"The more I think about it, the more crazy it was," the "Cool as Ice" artist added.
Ice and Madonna, 64, met in 1991 when she attended one of his concerts in New York City. The rapper recalled spotting the "Like a Virgin" singer in the crowd "dancing her ass off" -- and while he was excited to see her enjoying his music, he found her and her star power "intimidating."
At the time Winkle was in his early 20s while Madonna was in her early 30s.
"I remember she came back to the dressing room and said hello to me, and she kind of gave me the sexy eyes and I was like… 'I must be way, way mistaken on that,'" he said. After finding out her interest was real, they arranged a date at a steakhouse.
Ice said of dating one of the ‘90s biggest celebrities, "It got weird. And I didn't know what was going on… My whole life is a snowglobe. You think Justin Bieber had it crazy? You have no idea what I had to go through, holy moly… My snowglobe was shaken up."
Though people wouldn't know it from the outside looking in, the rapper said the two had a very "normal relationship."
"When you take away the [celebrity] factor… you have two people that have to deal with two people. It's just basically her and I, and at that point, it wasn't anything different than any other normal relationship," he explained.
After Madonna released her infamous erotic coffee table book titled "Sex" in 1992, Ice felt it was best for them to go their separate ways -- after the book featured explicit photos of him, allegedly without his consent.
"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," he admitted. "She was not happy with it and [was] upset."
Though the two didn't end on good terms, he called Madonna "great," "a legend" and "one of the greatest ever."