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Crystal Hefner Describes Her "Traumatic" Marriage to Hugh Hefner
Crystal Hefner has officially left the Playboy mansion behind.
The 39-year-old—who was married to Hugh Hefner from 2012 until his death in 2017—got engaged to her boyfriend of one year James Ward, 41, on April 25 at her Hawaii home, the couple confirmed to Us Weekly.
And the marine biologist’s proposal was completely unexpected for Crystal, who met James through mutual friends in 2024.
“It truly feels like a full-circle moment. James completely surprised me," she told Us Weekly in an interview published May 2. "He had a hidden staircase and a winding trail cleared to reveal a handcrafted deck perched above a dramatic cliffside overlooking the ocean.”
She continued, “It was the exact spot where we’d had a quiet picnic together a year ago—a place that became ‘ours.’ I had no idea he was secretly turning it into something permanent and symbolic. I thought we were just going for a walk, but when I saw the flowers, the handwritten notes, and the sea stretching endlessly in front of us, I knew something extraordinary was about to happen."
The couple noted they plan to “enjoy being engaged for awhile,” but are looking to tie the knot in 2026. And according to Crystal, they want to have an intimate ceremony that is “full of love, meaning and connection.”
James—who got down on one knee with a six-carat vintage ring—led Crystal to their proposal spot with a path of handwritten notes, which at first thought was birthday surprise, as it happened just four days before her 39th birthday and just after the pair had returned from a trip to Africa to celebrate their one-year anniversary.
"I was overwhelmed," she shared. "It was one of the most thoughtful things anyone has ever done for me.”
Instagram/Crystal Hefner
Prior to saying “yes” to James, Crystal was married to Hugh, who she was married to when he passed at 91-years-old. Seven years after his death, the former model revealed she was "never truly in love with him."
"It's hard to be in love with someone who wants multiple people in the bedroom," she admitted to E! News' Francesca Amiker in 2024, "and really only cares about themselves and their own needs and wants."
However, she also shared that had worked to move forward from the experience.
"I'm in a much better place," she said. "I feel that I will always be a work in progress, but I feel that I finally have true freedom."
For more recent celeb engagements, read on.
Photo by Noam Galai/Getty Images for Disney
Jacob Batalon
The Spider-Man actor spun a web of love as he popped the question to Veronica Leahov. Jacob confirmed his engagement with a March 5 post on Instagram that read, "The beginning of the rest of our lives together."
Instagram/Este Haim
Este Haim
Though the Haim member kept the details on her partner private, Este did confirm her engagment in a Feb. 13 Instagram post.
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Drake Maye & Ann Michael Hudson
The New England Patriots quarterback popped the question to his longtime love during a beach proposal. "Love doing life with you," he wrote on Instagram Jan. 15, sharing photos from the romantic moments. "Can't wait to marry you!"
Ryan Edwards / Instagram
Ryan Edwards & Amanda Conner
Three months after announcing that they are expecting their first baby together, the Teen Mom star proposed to his pregnant girlfriend during a snow family vacation. And he posted an adorable Instagram video Jan. 12 to commemorate the moment.
Cindy Ord/Getty Images for SiriusXM
Zendaya & Tom Holland
The Challengers actress hard-launched her engagement to her Spider-Man costar on Jan. 5, stepping out at the 2025 Golden Globes with a five-carat diamond ring by Jessica McCormack on that finger.
Tom's dad Dominic Holland later confirmed the couple's engagement, saying that his son "had everything planned out" for the proposal—including getting permission from Zendaya's father ahead of time.
Instagram/Montana Jordan
Montana Jordan & Jenna Weeks
Georgie is getting married! The Georgie and Mandy's First Marriage star announced his engagement to Jenna—with whom he shares daughter Emma Rae Jordan—on Jan. 5.
Chloë Grace Moretz & Kate Harrison
The Kick-Ass actress seemingly confirmed her engagement to the model in a Jan. 1 Instagram post, which featured photos of the duo's diamond rings.
Instagram/Jadejha Edwards
Jadejha Edwards & Darian Holt
The Circle costars announced their engagement on Jan. 1, sharing photos from the rose-filled proposal.
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