Vanilla Ice's dating history is short but sweet.
Born Robert Matthew Van Winkle, Vanilla Ice launched his career in 1989 with his debut album, Hooked. He released more albums while working as an actor and TV host.
He's held down a busy schedule as a rapper and actor, but had time to date over the years.
Vanilla Ice's Dating History
As of press time, Vanilla Ice only has four known relationships.
He was initially linked to Rowanne Brewer and Connie Hamzy, though the details about his time with both were never disclosed.
He had his first high-profile romance with Madonna afterward, and almost wed the Queen of Pop.
During his appearance on the Just Jenny with Jenny Hitt podcast in 2023, the "Ice Ice Baby" hitmaker revealed he once received a proposal from Madonna.
"Things were going so crazy and fast, man. I was just like, 'What? I thought the guy was supposed to do that,'" he recalled. "'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.'"
Vanilla Ice and Madonna reportedly met in the early 1990s when he watched one of her shows in New York City. Set up via SBK Records cofounder Charles Koppelman, the duo eventually had their first date.
"It got weird. And I didn't know what was going on... My whole life is a snowglobe," he went on. "You think Justin Bieber had it crazy? You have no idea what I had to go through, holy moly... My snowglobe was shaken up."
However, things hit rock bottom when she released her erotic coffee table book, S--, in 1992. According to Vanilla Ice, he realized it was best for them to part ways.
He went on to marry Laura Giaritta and stayed with her for nearly two decades. She filed for divorce in 2016.
READ ALSO: Pitbull Dating History: Rapper's Current Relationship Status, Ex-Girlfriends, Flings, MORE
Vanilla Ice's Show Dates
After Vanilla Ice's concert at Mar-a-Lago on New Year's Eve, the "Ninja Rap" rapper has yet to confirm his next show dates.
He previously joined the I Love The 90s Tour at the Big E Arena and SeaWorld summer concert series after canceling his shows when the COVID-19 pandemic started.
Vanilla Ice: What Does He Do Now?
In an Instagram post, Vanilla Ice hinted at his new podcast project with Steve-O. Dubbed Vanilla Ice Project, the new material seemingly references his reality TV series of the same name that was released in 2010.
The rapper has yet to share further details about the podcast.
READ MORE: Timbaland Dating History: Real Score With Nelly Furtado + Every Woman He Dated and Was Linked To
