Walking the red carpet with then-wife Mayte Garcia, Prince met the Prince of Wales at the De Beers and Versace "Diamonds Are Forever" charity fashion event on June 9, 1999. The star-studded shindig helped raise money for several organizations, including Charles' Prince's Foundation, which benefits architecture and the environment.
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Prince, who had celebrated his 41st birthday just two days before the event, was wearing a black and gold turtleneck and greeted the tux-clad Charles, then 50, on the red carpet.
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Other stars in attendance included actor Hugh Grant and his then-girlfriend Elizabeth Hurley.
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The iconic singer-songwriter died on Thursday. Prince's autopsy was completed on Friday, but his cause of death has yet to be revealed.
Of the loss of her former spouse, Garcia told PEOPLE, "This man was my everything, we had a family. I am beyond deeply saddened and devastated."
Garcia, who wed Prince at 22 in 1996, gave birth to the couple's son, Boy Gregory, in late 1996. The newborn only lived a week after being born with Pfeiffer syndrome, a rare genetic disorder that affects the skull and bones in the hands and feet.
Of the one-time couple, Lindsley Allen, a former dancer on Prince's The World In a Day Tour, told PEOPLE, "They had a great love for each other. They had a twinkle in their eye."