TBT: Nick Cannon Proposed to Mariah Carey With a 17-Carat Diamond Hidden in a Ring Pop Wrapper

Which is basically the size of an actual Ring Pop.

Who: Five-time Grammy winner, 21-time Billboard Music Award winner, and Songwriters Hall of Fame inductee Mariah Carey, 52, and actor, rapper, and comedian Nick Cannon, 42.

How They Met: Carey and Cannon first met in 2005 at the Teen Choice Awards, where the comedian — along with Ashlee Simpson — presented the “Butterfly” singer with the award for Best R&B Artist. And backstage, Mariah made a memorable impression on Nick that he remembered even a decade later.

"She had heard me speaking all of these positive, secret little nothings about her in interviews, and I remember seeing her backstage, and she stops right in front of me," he said in a clip from TV One's Uncensored in 2014. "She's like, 'I heard all those nice things you've been saying about me.' I was like, 'They're true! Just give me an opportunity to make them come true!' And she smiled, and they floated her off."

Nothing came of the flirty exchange (at least not initially) until April 2008, when Nick was cast as  Mariah’s love interest in her “Bye, Bye” music video. People began speculating that something was going on behind the scenes — and less than a month later, the rumors were confirmed to be true after the two secretly got married at Mariah’s mansion in the Bahamas. “We really do feel we are soulmates,” Carey told People at the time. “I never felt a love like this was in the cards for me.”

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Why We Loved Them: Out of all of the five love languages, Mariah and Nick’s was undoubtedly giving gifts, and ultra-extravagant ones at that.

Nick bought Mariah luxury cars (a custom pink Porsche Cayenne, Rolls Royce Phantom) despite her not even having a driver’s license, and, of course, lots of bling — including her  17-carat, $2.5 million engagement ring that was disguised in the wrapper of her favorite candy.

While hanging out on the rooftop of her Manhattan apartment, Cannon proposed to Carey with the massive diamond that was hidden in the packaging of a Ring Pop. “They’ve been calling me Cinderella since I first started out,” she told Elle of the fairy tale-worthy proposal. “Most people would think, Okay, please! This doesn’t happen in real life.”

When They Peaked: Speaking of fairy tales, on their fifth wedding anniversary, the happy couple renewed their vows at the happiest place on earth: Disneyland. Wearing matching prince and princess costumes, Mariah and Nick shut down the theme park for the lavish ceremony. Carey arrived at the Sleeping Beauty Castle in a horse-drawn, pumpkin-shaped carriage, before saying “I do” in front of 250 guests, which included Mickey and Minnie Mouse.

The Breakup: In 2014, the couple, who share twins Moroccan and Monroe, separated following six years of marriage, and Nick filed for divorce shortly thereafter.

The couple’s divorce took nearly two years to finalize, and according to Mariah, things got messy for a time. “Honestly, I think Nick and I could have worked it out between the two of us, but egos and emotions got inflamed (which can translate into many billable lawyer hours, and ultimately it did),″ she wrote in her book, The Meaning of Mariah Carey. “It was tough. We both wanted to make sure everything was cool for our family. We will always be family, and we make it work.”

As for Nick, he realized that he is “not built for marriage” after he and Mariah split. In 2022, he admitted that he hasn’t fully healed from the divorce, explaining: “Divorce is a sense of, 'You failed,' and when you have that level of failure with everyone seeing it, it was a lot on me for a long time," he said. "I didn't really know how to process it. I had to go find myself. I had to go within."

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Where They Are Now: A year after her split from Cannon, Carey began dating Australian billionaire businessman James Packer. Months later, they got engaged, with James popping the question with a $13.2 million diamond ring. The engagement was short-lived, however, and the two called it quits in October 2016. Today, Mariah is in a relationship with her backup dancer Bryan Tanaka.

Following her split from Cannon, Carey turned her focus back to music. The year of their separation, she came out with her 13th studio album, Me. I Am Mariah. and went on tour. Since then, she's released five more albums — including two Christmas ones — and this month, the queen of Christmas will host four holiday-themed shows as part of her Merry Christmas To All tour. CBS will air the two-hour concert special on Dec. 20.

Since his relationship with Carey ended, Cannon has adopted a polyamorous lifestyle and welcomed nine children with five different women. His primary relationship is with model Abby De La Rosa, and the two share 16-month-old twins — Zion Mixolydian and Zillion Heir — and De La Rosa is pregnant with the couple's third child.

On the professional front, Cannon is busy with his roles as executive producer and host of Fox's The Masked Singer, executive producer of the comedy show Wild ‘N Out, as well as the host and producer of his own radio show Nick Cannon Radio. 

#TBT: Check in every Thursday as we throw it back to some of our favorite celebrity couples of all time.

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