Crystal Hefner, 39, widow of Playboy founder Hugh Hefner is engaged to Hawaiian businessman James Ward, 41, after one year of dating. Ward proposed on April 25, 2025, at Crystal’s Hawaii home with a six-carat vintage mine-cut diamond ring.
The surprise unfolded on a handcrafted seaside deck Ward built, overlooking a cliff where the couple had picnicked a year prior. “I thought we were just going for a walk” Crystal told Us Weekly. Handwritten notes lined a hidden staircase leading to the final message. “I was already crying by the last note,” she said, initially mistaking it for a birthday surprise.
Crystal, who met Ward through mutual friends in April 2024, described the moment as “full-circle.” Ward, a marine biologist and owner of SeeThrough Sea, a Kailua-Kona adventure tour company, used her maiden name, Crystal Margaret Harris, during the proposal, honoring her identity. “James supports me being Crystal Harris. I’ll never lose my identity again,” she told DailyMail.com. The couple plans a 2026 wedding, eyeing a tropical setting like Hawaii or the Cook Islands, keeping it “simple and beautiful.”
Crystal married Hugh Hefner in 2012 at age 26, while he was 86. Their marriage, marked by a 60-year age gap, lasted until his 2017 death at 91 from heart failure and septicemia.
In her 2024 memoir, Only Say Good Things: Surviving Playboy and Finding Myself, Crystal revealed she never loved Hefner, describing emotional abuse and a “power imbalance” at the Playboy Mansion. Under their prenup, she inherited a $5 million home and jewelry but none of his $43 million fortune.
Post-Hefner, Crystal relocated to Hawaii, where she found healing. “I’ve done a lot of necessary healing since the mansion,” she told Us Weekly.
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Ward, unlike past relationships, offers validation and protection. “I feel accepted and more myself than ever,” she said. Their shared love for nature and adventure, seen in trips to Africa and the Cook Islands, cements their bond. No wedding date is set, but the couple aims for an intimate, nature-filled ceremony.
