Crystal Hefner Is Engaged to James Ward Following One Year of Dating

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.”

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.

The RuPaul's Drag Race All Stars season two winner announced that she and partner Matthew Herrmann are engaged.

"My longtime partner Matthew Herrmann proposed to me yesterday," the reality star, who was runner-up on season five, told Entertainment Weekly in a statement Aug. 4. "It was after my grandma's 90th birthday celebration."

 

Fashion designer Diane von Furstenberg announced that her granddaughter and longtime boyfriend, Rocco Brignone, got engaged after nearly seven years of dating. 

“Talita and Rocco are ENGAGED!!!” Diane, 78, wrote on her July 31 Instagram post, which features a sweet photo of the couple glowing after the proposal. “He proposed. She accepted! Join me in wishing them a happy joyful life together. LOVE is LIFE.”

Talita confirmed the romantic news on her Instagram shortly, writing, “Forever!!!!!!!!!!!! I love you so much my heart is bursting.”

The Indiana Pacers player popped the question to his college sweetheart at their alma mater.

"The place where our story started," he wrote on Instagram July 28, sharing photos and video from the romantic proposal inside Illinois State University's Hilton Coliseum, "and where our next chapter begins."

The Zac Brown Band frontman and the jewelry designer announced their engagement in July 2025, just two months after they debuted their relationship at the American Music Awards.

"We are so happy and grateful, the couple told People at the time, "that we found each other."

The tennis star confirmed her engagment to the Italian actor following her July 22 win at the Mubadala Citi DC Open, crediting him with her return to the court.

"He encouraged me to get through this," she said, "and it’s wonderful to be here. He’s never seen me play."

The You actress casually dropped the news July 21, writing on Instagram, "It’s no secret I’m deeply in love or that I’m engaged to Ethan. I tell everyone I meet."

The Love Island UK alums got engaged after finding love on season 11 of the series. Uma Jammeh, who left the villa after Wil Anderson was dumped from the island, wrote on Instagram July 14, "We’ve been sitting on a bad boy piece of information."

On July 11, the Disney Channel announced she got engaged to the basketbal player after he proposed poolside at an oceanfront resort. 

Nicola Peltz Beckham’s older brother and the late Quincy Jones’ youngest daughter confirmed their engagement after more than a decade together. 

“JUST ENGAGED,” Kenya captioned the July 9 Instagram post featuring a black and white photo of the couple kissing on a boat. “My whole heart for my whole life.”

After seven years of dating, the singer-songwriter proposed to the Bachelor alum in Mallorca. Hayley shared a photo of the picture-perfect moment in a July 10 Instagram post, writing, "My dream girl said yes forever..."

While their romance first blossomed in 2018, the pair kept their relationship private until May 2022. "We've been together for four years," Becca told E! News in 2022. "So the good thing is when we went public, we felt very solid in our relationship."

The Entourage alum proposed to the If Loving You Is Wrong actress on Fourth of July during a family celebration in Long Island, N.Y. 

The Fashion Police alum was surprised with an engagement ring from the Slipknot member during her dad Ozzy Osbourne's final Black Sabbath show on July 5. The proposal was witnessed by friends and family, including Kelly's mom Sharon Osbourne, brother Jack Osbourne as well as her and Sid's son Sidney.

He may have failed to win the heart of Rachel Lindsay, but the Bachelorette alum did end up getting his happily ever after. He proposed to his girlfriend in July after one year of dating, writing on Instagram, "Throughout it all, it was always you. I just had to find you. I love you."

The Big Time Rush singer and his longtime partner announced their engagement May 15.

The Vampire Diaries alum and The Originals actor prove that they're a fang-tastic match, announcing their engagement on May 14.

As seen on the May 13 episode of1000-Lb. Sisters, the TLC star got engaged to her boyfriend of five months after he proposed inside a haunted house. 

The star of Marvel's Shang-Chi and the Legend of the Ten Rings and his longtime partner announced their engagement May 11.

Seven years after the death of Hugh Hefner, his widow got engaged on April 25 at her Hawaii home. 

The Dancing With the Stars alum got engaged to the singer during a Hawaiian vacation in late March, with Frankie writing on Instagram, "13 years in the making."

Fifteen years after making headlines as one of Tiger Woods' mistresses in his marrige to Elin Nordegren, the former Las Vegas hostess announced her engagement to her businessman boyfriend on March 28.

Bruce Willis and Demi Moore's daughter got engaged to the musician, writing on Instagram March 23 alongside a photo of her 4-carat diamond bling designed by Karina Noel, “Never knew a ring could encapsulate a love so perfectly."

 

The YouTuber-turned-boxer announced his engagement to the Olympic speed skater on March 22, sharing photos of himself proposing on a balcony overlooking the water on Instagram.

The Spider-Man actor spun a web of love as he popped the question to the architectural designer, confirming his engagement with a March 5 Instagram post that read: "The beginning of the rest of our lives together."

Though the Haim member kept the details on her partner private, she did confirm their engagment in a Feb. 13 Instagram post. 

The Laguna Beach alum announced her engagement to the investor on Jan. 21, writing on Instagram, ""For you, my darling, it could only be a 'yes.'"

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!"

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.

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.

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.

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.

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