Hugh Hefner’s love life was unconventional, but his marriage to Crystal Hefner seemed to normalize him ahead of his September 2017 death.

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

“I tried marriage twice before but there’s no comparison,” Hugh exclusively told Us Weekly in January 2014 of his marriage to Crystal. “This is the real deal. And to find true love at this age? It’s 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 up his life and home to the world,” she told 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 exclusively told Us in August 2023, while teasing her 2024 memoir, Only Say Good Things: Surviving Playboy and Finding Myself. “You start backtracking 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, understand myself and also 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 twosome met when Crystal was 21 when she attended a Halloween party at the Playboy Mansion. That same month, she was named “Co-Ed of the Month” on Playboy.com.

October 2009

Crystal made her debut on Girls Next Door while living with Hugh and twins Karissa and Kristina Shannon. Crystal became Playboy’s Playmate of the Month two months later.

December 2010

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

June 2011

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

“[Sex lasted] like, two seconds,” she quipped. “Then I was just over it. I was like, ‘Ahh.’ I was over it. I just, like, walked away. I’m not turned on by Hef. Sorry.”

Hugh fired back at Crystal’s claims via social media at the time, alleging, “For the record, I have sex on a weekly basis. And I did throughout my two-and-a-half years with Crystal.”

June 2012

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

December 2012

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

February 2013

After slamming Hugh’s sexual prowess during their brief breakup, Crystal played coy about their sex life once married. “I feel like since Hef is older now and he’s had . . . the phases of all the girlfriends and all that kind of stuff . . . I feel now is more, you know, like cuddling up and watching a movie or playing backgammon,” she told HuffPost Live. “We play Uno with the girls.”

January 2014

“I think the center of her life is us and you can’t ask for more than that,” Hugh exclusively told Us of his marriage to Crystal. “With the age disparity, I’m a very lucky cat. I’m very, very happy.”

December 2014

Crystal gave fans an inside look at the holidays in the Hefner house via a YouTube video. “We celebrate Christmas Eve and Christmas Day. Like for gifts … Hef and I, we’ll open gifts Christmas Eve,” she shared. “So it’s kind of nice to do that because first off, it’s a day early. And second, you get Christmas just to hang out and relax and not have to worry about gifts and things like that. So it works out. I like that tradition.”

Crystal added, “It’s the best time of year not just ’cause of gifts and stuff, but because of my friends and because of [my Christmas tree] and because it’s just such a cozy 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, telling Us in October 2017, “I haven’t been able to bring myself to write most people back to thank them for their condolences. I am heartbroken.”

She continued, “I am still in disbelief. We laid him to rest Saturday. He is in the place he was always certain he wanted to spend eternity.”

Crystal gushed over her late husband, adding, “I will feel eternally grateful to have been by his side, holding his hand, and telling him how much I love him. He changed my life, he saved my life. He made me feel loved every single day. He was a beacon to the world, a force unlike anything else.”

August 2023

Crystal recalled what it was like moving into the Playboy Mansion just days after meeting Hugh. “Going in, I was a deer in the headlights. It was like I just got the golden ticket for the Willy Wonka [factory],” she exclusively told Us, while teasing her upcoming memoir. But eventually, she added, “It all started crumbling down.”

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 value of my own,” she claimed. “You’re rewarded for not having a life of your own outside of the person. I’ve learned a lot about self-worth, self-love, advocating for yourself and healthy relationships.”

Thank You!

You have successfully subscribed.

Crystal added that she thinks Hugh would have been supportive of her speaking her truth so publicly. “I hope that being such an advocate for freedom of speech, that [Hugh] would be an advocate for me telling my story,” she concluded. “Women’s voices are getting louder, and that’s really important.”

January 2024

“I realized I was dealing with a really big power imbalance,” Crystal told People, revealing she was never “in love” with Hugh. “It seemed like a world of success and fantasy, but everyone’s having to sleep with an 80-year-old. There’s a price. Everything has a price.”

ncG1vNJzZmivp6x7tr%2FMmp6aspmjsm%2BvzqZmnJ2cmq%2BztdOyZKedp6h8r7HWrGahrZedeqmxxaecq2WRo7Fuf9GdZLChlpp6pL7YrKuapF2dsqe6xKuqZqqVoa61tc6nqqGhoGLBqrnEpaCnnV8%3D