Hugh Hefner’s Widow Crystal Hefner Get Engaged!

Crystal Hefner finds love again with tour entrepreneur James Ward, who proposed with a six-carat diamond at the same Hawaiian cliff where they once picnicked — a symbolic full-circle moment after her past with Playboy founder Hugh Hefner.

May 3, 2025: Crystal Hefner is ready to say “I do” once again — this time to James Ward, nearly eight years after the passing of her late husband, Playboy founder Hugh Hefner.

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The 39-year-old author and former model got engaged on April 25 at Hefner’s former home in Hawaii, in a deeply personal and symbolic proposal. According to Us Weekly, Ward surprised her with a six-carat vintage mine-cut diamond ring on a handcrafted deck overlooking the ocean — the same scenic cliffside where the couple once enjoyed a quiet picnic.

“It truly feels like a full-circle moment,” Crystal shared. “I had no idea he was secretly turning our special place into something permanent and symbolic.”

Ward, 41, who runs See Through Sea tours, said keeping the proposal secret wasn’t easy.

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“It runs so contrary to our connection to keep anything from her,” he told People, adding, “But knowing how happy the surprise would make her made it so worthwhile.”

Crystal had earlier gushed about her relationship with Ward, whom she began dating in April 2024 after a mutual introduction. In September, she noted the emotional contrast between her new romance and her past marriage to Hugh Hefner.

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“With James, my feelings are valued, validated. I am seen and I am heard,” she said.
“I feel accepted and more myself than ever before.”

Crystal was married to Hugh Hefner for five years before his death in 2017 at the age of 91. Her engagement to Ward not only marks a new chapter in her life but symbolizes a healing journey toward love and self-discovery.

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