Vanilla Ice claims that ex-girlfriend Madonna once proposed to him

“Vogue” superstar Madonna has had a string of number-one hits spanning over 40 years, but sometimes her personal relationships have made just as many headlines as her chart-topping smash tunes. 

Apart from her two marriages to Sean Penn and Guy Ritchie, she has been linked to Dennis Rodman, Warren Beaty, Tupac Shakur, Alex Rodriguez, and many more … including “Ice Ice Baby” rapper Vanilla Ice in the early 90s.

Yes, the man who wanted us all to "stop, collaborate, and listen" was once the beau du jour of the Material Girl. Did you forget that they were once an item? Because he sure hasn’t. Over the years he has made it a point to frequently talk about his relationship with the “Hung Up” songstress. And today is one of those days where, yes, he’s revealing new and private details about their time together, alleging that she popped the question to him despite their age difference. 

“Things were going so crazy and fast, man. I was just like, ‘What?!’” he told Just Jenny with Jenny Hutt podcast on Tuesday. “‘I thought the guy was supposed to do that [propose]. 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!’” 

“So, yeah. It was crazy. The more I think about it, the more crazy it was.”

For 30 years, the one-hit wonder and Dancing On Ice contestant has made their short-lived fling a talking point in almost all of his press interviews. And often, he includes some wild claims about their time together.

How they first hooked up

Back in 1991, Madonna’s provocative tour documentary, Madonna: Truth or Dare, was about to change the face of rockumentaries forever. At the premiere, rapper and pantsuit aficionado Vanilla Ice made an appearance on the red carpet. Although Madge and the rapper weren't seen together at the event, they later did a flirty and funny skit together when the "La Isla Bonita" singer accepted a Smash Hits award. It seems they were off to the races after that.

What their time together was like

According to Vanilla Ice, they had a gas trying to go out on movie dates unrecognized. On George Stroumboulopoulos Tonight, he recalled, "I had a mustache and hat with hair coming down, and she would go as an old lady." He also called their fling a "normal relationship."

He reiterated that to Jenny Hutt, saying, “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.”

Why he says their relationship didn’t last

If there was a problem (yo!), he solved it by breaking up with Madonna when compromising photos of the two appeared in her notorious 1992 "Sex" book. We warn you, his comments haven’t aged well

"I was hurt to be an unwitting part of this slutty package," he told News of the World. "It was disgusting and cheap ... 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." 

His slut-shaming comments may have been fair game in the '90s, but not these days. Despite that, he still doubles down on that belief. Speaking with host Jenny Hutt, he said, “So, that book came out, and I thought it was so slutty. I didn’t want to be a part of it. 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 and I go mine.’” 

“And she called me all the time and she was not happy with it and upset and I’d have to hang up on her a few times, but that was it.”

He was obsessed with their age difference

After the “Open Your Heart” chart-topper and Vanilla Ice called it quits, the rapper would harp on their age difference, telling News of the World, "She was older than me and a great lover. She's still the oldest person I've ever been with, so it was an experience." Later he told USA Today in 1994, "She's got a great body for her age.”  YIKES. 

Quite often, Madonna’s boyfriends have been much younger than her, despite the frequency of older men in Hollywood dating younger women. She told Harper’s Bazaar in 2017, “I have lovers who are three decades younger than me. This makes people very uncomfortable. I feel like everything I do makes people feel really uncomfortable."

These days, Vanilla Ice is a bit kinder to the Queen of Pop

These days, the Cool as Ice star has changed his tune … somewhat. He told George Stroumboulopoulos during an appearance on the host's eponymous show that the "Ray of Light" singer was actually "a sweetheart." When confronted in 2011 by paparazzi for comment on Elton John's beef with Madonna over her beating him in the best original song category at the Golden Globes, the "Ice Ice Baby" rapper actually came to her defense, insisting that she deserved to win.  

Yesterday speaking on the Just Jenny with Jenny Hutt podcast, he reiterated those feelings, calling her  “great,” “a legend,” and one of the greatest ever.”

@etalkctv Did you know that Madonna proposed to Vanilla Ice back in the ‘90s? The rapper opened up about his whirlwind relationship with Madonna on the Just Jenny with Jenny Hutt podcast. He shared how shocked he was that the pop icon wanted to go on a date with him due to his young age, how they met, and how she broke social norms by proposing to the “Ice Ice Baby” rapper. Why did they not get engaged? He blamed that things were moving too fast. (🎥: YT/ @Jenny Hutt ) #vanillaice #madonna #engagement #hollywoodcouple #throwback ♬ original sound - etalk

Madonna has a sense of humour about it all

The “Justify My Love” singer on the other hand, has made a point of poking fun at Vanilla Ice. Speaking with Us Weekly in 2015, the pop icon quipped, "If 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 humour. Plus, he could always wear my clothes."

The Queen of Pop hasn’t responded to his latest interview, probably because she’s too busy planning her upcoming world tour “Celebration.”