EXCLUSIVE: Vanilla Ice Dated Madonna at 20 (She was 30), Broke Up After She Released Their Dirty Pics

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Vanilla Ice opened up about his brief but intriguing relationship with pop icon Madonna. The rapper, then 20, met Madonna, who was 30, at one of his shows at Madison Square Garden in New York. Describing Madonna as a "sweetheart" and a legend, Vanilla Ice reminisced about how the megastar joined him in his dressing room and even danced energetically throughout his performance. Their relationship soon turned serious, evolving into what he called a "normal relationship between two people." However, their romance hit the rocks after Madonna released a controversial photo book, which included intimate pictures of the couple. Disapproving of the public display of their private moments, Vanilla Ice broke up with the star. Despite their split, he expressed respect for Madonna, sharing that their time together was memorable but ultimately overshadowed by the scandalous photo release.