The relationship timeline of Hugh Hefner and third wife Crystal Hefner

Hugh HefnerHis love life was unconventional, but his marriage to Crystal Hefner seemed to normalize him prior to his death in September 2017.

The Playboy mogul was married twice before he and Crystal tied the knot in December 2012 and was the father of four adult children. While he and Crystal had a rough road to the altar, Hugh had only good things to say about his wife after their one-year anniversary.

“I've tried marriage twice before, but there's no comparison,” Hugh said exclusively We weekly in January 2014 from his wedding to Crystal. “This is the real deal. And to find true love at this age? It is remarkable.”

When Hugh died at the age of 91, Crystal mourned his loss by singing his praises. “He was an American hero. A pioneer. A kind and humble soul who opened his life and home to the world,” she said Us in a statement in October 2017. “I felt how much he loved me. I loved him so much.”

Years later, Crystal hinted that her marriage wasn't always perfect. “Therapy really helped [me process my trauma],” she shared exclusively Us in August 2023, teasing her 2024 memoir, Only say good things: Surviving Playboy and finding myself. “You start walking back and [noticing] different behaviors. I'm like, 'Oh, that's gaslighting. That's narcissism.' It took years for me to understand what I went through, to understand myself and also to understand Hef and why he did certain things. You know, there's a story behind everything.”

Scroll down to see Crystal and Hugh's ups and downs:

October 2008

The pair met when Crystal was 21 when she attended a Halloween party at the Playboy Mansion. That same month, she was named Playboy.com's “Co-Ed of the Month”.

October 2009

Crystal made her debut on Girls next door while living with Hugh and twins Karissa And Kristina Shannon. became crystal Playboy's Playmate of the Month two months later.

December 2010

Hugh proposed during the holidays. “When I gave Crystal the ring, she burst into tears,” he wrote at the time via X (then Twitter). “This is the happiest Christmas weekend ever.”

June 2011

Just days before they were set to walk down the aisle, Crystal called off the wedding. In July 2011, Crystal addressed her former fiancé and their sex life while on Sirius XM's. Howard Stern Show.

“[Sex lasted] two seconds,” she joked. “Then I was just over it. I thought, 'Ah.' I was over it. I just walked away. I'm not turned on by Hef. Sorry.”

Hugh fired back at Crystal's claims on social media at the time, claiming: “For the record, I have sex every week. And I did that during the two and a half years at Crystal.”

June 2012

A year after calling off their engagement, Crystal confirmed that she and Hugh were back together. “Yes, I'm his number 1 girl again. Yes, we are happy,” she wrote via X. “Hope this clears up any confusion! XO.”

December 2012

Us confirmed that the couple tied the knot on New Year's Eve at the Playboy Mansion in Los Angeles.

February 2013

After criticizing Hugh's sexual prowess during their brief breakup, Crystal played coy about their sex life after they got married. 'I feel like Hef is older now and he…' . . the phases of all the girlfriends and all that stuff. . . I feel like it's more now, like cuddling and watching a movie or playing backgammon,” she said Huff Post Live. “We're playing Uno with the girls.”

January 2014

“I think we are the center of her life and you can't ask for more than that,” Hugh shared exclusively Us of his marriage to Crystal. “Considering the age difference, I am a very lucky cat. I am very happy.”

December 2014

Crystal gave fans a glimpse into the holiday at the Hefner house via a YouTube video. “We celebrate Christmas Eve and Christmas Day. Like for presents… Hef and I, we open presents on Christmas Eve,” she shared. “So it's kind of fun to do that because first of all it's a day early. And secondly, you get Christmas just to hang out and relax, without having to worry about gifts and stuff like that. So it works. I love that tradition.”

Crystal added, “It's the best time of the year, not just because of gifts and stuff, but because of my friends and because [my Christmas tree] and because it is just such a fun holiday. I love it. Christmas is my favorite holiday!”

September 2017

Hugh died at the age of 91. His widow mourned the loss in the weeks that followed, tellingly Us in October 2017: “I haven't been able to bring myself to write back to most people to thank them for their condolences. My heart is broken.”

She continued, “I'm still in disbelief. We laid him to rest on Saturday. He is in the place where he was always sure he wanted to spend eternity.”

Crystal gushed over her late husband, adding, “I will be forever grateful that I stood by his side, held his hand and told him how much I love him. He changed my life, he saved my life. He made me feel loved every day. He was a beacon to the world, a force unlike anything else.”

August 2023

Crystal recalled what it was like to move into the Playboy Mansion just days after meeting Hugh. “When I went in, I was a deer in the headlights. It was like I had just gotten the golden ticket to the Willy Wonka [factory],” she shared exclusively Us, while teasing her upcoming memoir. But eventually, she added, “it all started to crumble.”

Crystal, who moved from Los Angeles to Hawaii after Hugh's death, noted that she wanted to “have a voice” and tell her story her way, including what it was like living among Playboy bunnies. “Your value is what you look like. I was rewarded for being codependent and feeling like I was nothing without Hef and had no worth of my own,” she claimed. 'You are rewarded because you don't have your own life outside the person. I learned a lot about self-esteem, self-love, standing up for yourself and healthy relationships.”

Crystal added that she thinks Hugh would have supported her if she spoke her truth so publicly. “I hope I am such an advocate for freedom of expression [Hugh] would be an advocate for telling my story,” she concluded. “Women's voices are getting louder, and that is very important.”

January 2024

“I realized that I was dealing with a very large power imbalance,” Crystal said People, which revealed that she was never “in love” with Hugh. “It seemed like a world of success and fantasy, but everyone has to sleep with an 80-year-old. There is a price. Everything has a price.”