“Everybody talks about having kids [in relationships],” the Wild ‘N Out host — who is the father of 12 children with six different women — told The Shade Room in March 2023, acknowledging that his next comment was about to go viral. “When Christina Milian and I were doing Love Don’t Cost a Thing, I remember when I found out she was pregnant [years later] … I was like, ‘Dang, man.’”
Despite Cannon’s regret about not having children with the “Dip It Low” singer — who shares daughter Violet with ex-husband The-Dream and sons Isaiah and Kenna with husband Matt Pokora — “I was so happy for her,” he added. “I remember we [were] kids in love early on, and so we talked about that. But to each his own. Life plans it out. The universe gives it how it’s supposed to be given.”
As Cannon and Milian’s Love Don’t Cost a Thing characters fell in love on screen in the 2003 remake of Can’t Buy Me Love, the actors entered a relationship real life as well, dating for more than two years before ultimately calling it quits in 2005.
“I was wrong for not being what she wanted me to be,” the Masked Singer host said in an interview one year later. “She knew from the jump. We were friends for months before we even got into it, and when we got into it, I was like … ‘Yo, anything remotely like a relationship, I don’t want no parts of it.’”
“The next thing you know, I was reading [everything]. For, like, a month, I was reading messages. It was unreal that it was happening. He was living at my house. … It was just like, ‘Wait, under my roof this is happening?’ It just kind of blew me away.”
Cannon, for his part, went on to have his own large family and several non-traditional relationships. He married Mariah Carey in 2008 and welcomed twins Moroccan and Monroe in April 2011. The couple divorced in 2016.
The All That alum shares 10 more children with five different women in short succession. He and Brittany Bell welcomed son Golden Saigon in February 2017 and daughter Powerful Queen in December 2020. Their third child, son Rise Messiah, was born in September 2022. Abby De La Rosa — who defended her polyamorous relationship with Cannon in 2022 — welcomed twin boys, Zion and Zillion, with the actor in June 2021. One year later, De La Rosa gave birth to their daughter, Beautiful Zeppelin, in November 2022.
Cannon also had two children with Alyssa Scott. Tragically, their son Zed died in December 2021 from brain cancer at 5 months old. One year later, they welcomed daughter Halo Marie. The Nickelodeon alum is also father of son Legendary Love, born in July 2022, with Selling Sunset star Bre Tieisi, and daughter Onyx, born in September 2022, whom he shares with LaNisha Cole.
Keep scrolling to see Cannon and Milian’s relationship timeline: