Inside Crystal Hefner's Relationship With Hugh Hefner

Hugh Hefner met the woman who would go on to be his final wife, Crystal Hefner, née Harris, at a Halloween party at the Playboy mansion in 2008. Crystal moved in the day after the pair met, and lived with Hugh alongside twin sisters Kristina and Karissa Shannon. Eventually, those two moved on, and Crystal and Hugh got engaged.

What followed next was a whirlwind of will-they-or-won't-they, as Crystal and Hugh called off their marriage in 2011, giving different accounts about what happened. While Hugh simply claimed on Twitter that Crystal had experienced a "change of heart," Crystal was much more forthcoming about her problems with the relationship. While speaking to Howard Stern in 2011, Crystal directly implied that the physical side of the two's relationship was less than satisfying, though she later walked those statements back (via HuffPost).

Whatever qualms they might have once had, Crystal and Hugh married in 2012 and were together for the rest of Hugh's life; his 2017 death left his wife stunned and unsure of where to go with her life next (per the Mirror). Here's a look at a relationship that surprised and mystified, and that contains multitudes of layers to dig through.

Crystal Hefner was only 22 years old to Hugh Hefner's 82 years old when the pair were introduced at Hugh's 2008 Halloween party. Despite that age difference, the two clearly hit it off. At the time, Hugh had three women — former girlfriends Holly Madison, Bridget Marquardt, and Kendra Wilkinson — living at the Playboy mansion, and Crystal later told The Futon Critic that she never imagined she would eventually end up moving in to take their place.

As Crystal explained to the publication, there was a lot to learn about Hugh and his lifestyle. She said, "The other three girls were still living here when I first met Hef so I had no idea what was going on but it was so fun and I was just living for the moment. Now I'm here and it's so much fun."

Crystal wasn't the only girlfriend in the mansion when she moved in. In fact, she shared her future husband with twin sisters Karissa and Kristina Shannon, but she told The Futon Critic that doing so wasn't really hard for her. As she said at the time, she had an idea of what to expect. She explained, "Hef explained his lifestyle ahead of time so when I came in here I knew either I'd like it or not. I like it and love everyone around."

The 60-year age difference between Hugh Hefner and Crystal Hefner definitely caused a few raised eyebrows, and it's probably not too surprising that some people believed the 22-year-old was only interested in Hugh for his vast Playboy-related fortune. Crystal later told The Sun that she was hit with attacks from just about everywhere, with people over-analyzing nearly every aspect of her character and her relationship with Hugh. As she put it, "I would get hit with all the stereotypes. People would say I was a dumb blonde, a fake, a gold-digger who didn't really love Hef. I suffered attacks on my relationship with him, on my looks, on my intelligence.'"

Despite all the negative energy being thrown at her, Crystal persevered and joined the cast of "The Girls Next Door" after moving into the mansion. As she told The Futon Critic, her goal was just to be herself and hope that people eventually warmed up to her. She said, "I just want to be me and just be real and just be myself and then hopefully the viewers can relate to that so that's what I'm hoping."

Crystal Hefner and Hugh Hefner got engaged on Christmas Eve in 2010. Hugh was quick to announce the news on Twitter, with Reuters reporting that he tweeted, "When I gave Crystal the ring, she burst into tears. This is the happiest Christmas weekend in memory." The marriage was Hugh's third and Crystal's first.

However, things didn't kick off right away. In fact, Crystal called off the wedding. The first time she ended things between the two was in June 2011, when Hugh again returned to Twitter to announce, "The wedding is off." TMZ added fuel to the fire, claiming that Crystal had moved out of the pair's home following an argument. As TMZ noted, the news broke only five days before the two were supposed to get married in the first place. 

Crystal later explained to Entertainment Tonight that Hugh's lifestyle was the reason why she ended things, explaining, "I wasn't the only woman in Hef's life. I didn't feel comfortable in my heart knowing that and getting married to him, because a marriage is between two people" (via the Daily Mail). She also added that having to work with lawyers to iron out a pre-nuptial agreement was stressful, explaining that she had never needed a lawyer before that experience. Ultimately, it sounds like Crystal had to make a decision that felt good to her, despite the estimated $250,000 loss cancelling the wedding leveled at Hugh.

Eventually Crystal Hefner and Hugh Hefner reconciled and went ahead with their wedding on December 31, 2012. As shared by The Sun, the pair reunited after Hugh's secretary reached out to Crystal and told her that he hadn't gotten over her; Crystal told the publication that when she finally agreed to meet up with Hugh again, she realized he was a changed man. As she said, "When I went back in 2011 the most beautiful woman you'd ever see would walk in with everything on display and Hef would say 'Have you met my wife Crystal?'"

Crystal also shared details about the wedding, including that her family attended alongside Hugh's four children. The Sun notes that the relationship seemed very positive and strong in the beginning, and Crystal explains that Hugh's turnaround made everything much better. As she put it, "Hef had realized what was most important in life, even it took him until he was 85. And he treated me completely different for the rest of his life. He treated me with respect."

Of course, marrying Hugh came with a set of rules and expectations, particularly some that were in place to safeguard his massive fortune. Us Weekly noted that Crystal was required to sign an "iron-clad" pre-nuptial agreement, with a source telling the publication his will dictated his money would go to "his children, the University of Southern California film school and a variety of charities."

Hugh Hefner certainly seemed like a change man after he and Crystal Hefner got married. In January 2014, he waxed poetic about their marriage, telling Us Weekly that his wife put their relationship first before everything else. As he said, "I think the center of her life is us and you can't ask for more than that. With the age disparity, I'm a very lucky cat. I'm very, very happy."

Hugh went on to add that despite having experienced marriage twice, this time around with Crystal was extra special. Hugh even added that he felt he had found "true love" with his young wife, something he admitted he didn't not expect to do so late in life. As he put it, "It's wonderful. It's better than anything I could possibly imagine."

It certainly does seem that Crystal returned a genuine love for Hugh. Ahead of their wedding, she told Piers Morgan in an interview that fun was at the center of their union and a big part of what drew her to her husband-to-be. She explained, "I love Hef. He's the nicest person I've ever met in my entire life. I have so much fun with him."

Hugh Hefner's unexpected death from sepsis in 2017 left Crystal Hefner a widow while she was still in her 20s, and that experienced offered her the opportunity to reflect on her life and marriage with Hugh. She explained to the Daily Mail that the pair were so wrapped up in one another that after Hugh died she felt lost, saying, "I didn't know how to move forward because I had become so ingrained in his world and I didn't even know my own identity."

Crystal added that the marriage wasn't always easy, and that at least once Hugh told her if she began to have a life outside of their marriage, the marriage would cease to exist. As she put it, this meant she really leaned on her relationship hard, noting, "I came to rely on him so much that I didn't really have a life outside of him. At one point he told me, 'When you start doing things away from the relationship, that's when it ends'" (per the Daily Mail).

Following his passing, Crystal felt she was so "ingrained in his world" that she wasn't sure what to do next. While admitting that she became "someone else's identity for 10 years," she shared that moving on after his death was scary, but was also the right thing to do. 

As shared by TMZ, Hugh Hefner was laid to rest on September 30, 2017, during a ceremony that was only attended by Crystal Hefner, a few members of Hugh's staff, and his four children: Christie, David, Marston, and Cooper. Hefner was buried at Westwood Village Memorial Park in Los Angeles.

While burying her husband was likely a terribly sad event for Crystal, she was able to rally and offer a truly moving statement to People following the experience. After explaining that the media mogul taught her so much, she added that being in a relationship with him had helped her in a number of ways, saying, "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."

Crystal also thanked the many people who had reached out to offer their condolences, apologizing for not having yet been able to reply to each of them. As she told People, the loss of her husband was just too much for her. She said, "He was a beacon to the world, a force unlike anything else. There never has and never will be another Hugh M. Hefner."

Celebrity Net Worth estimated that Hugh Hefner was worth a stunning $50 million at the time of his 2017 death. As his wife, many assumed that Crystal Hefner would be left with the bulk of that fortune — but Hugh left most of his money to his children and charity. The reality of the matter is that Crystal was legally obligated to a $7 million payout and also walked away with a property Hugh had bought her worth $5 million (per the Daily Mail). While this certainly left her with plenty of money, it was a far cry from one might have assumed. The Daily Mail also valued Crystal's engagement ring at $50,000.

Celebrity Net Worth also noted that at one point, Hugh was actually worth around $200 million, but disappointing magazine sales during the final 10 to 15 years of his life brought that number down. 

On January 10, 2022, Crystal wrote in an Instagram post, "I was living for other people before, to make others happy, suffering internally in the process." After spending over a decade involved in the world of Playboy, per Insider, Crystal is now in the process of reconnecting with who she really is.

Alongside Instagram posts of her travels to places like Egypt and the Maldives, Crystal regularly shares introspective statements about her life. In one post, she said, "My photos may all look super polished but I'm still figuring it out. Still figuring out who I am. What I want to do. The direction of my life." Part of her new journey involves removing "everything fake" from her body, as well as deleting older photos of herself that she no longer connects with. By making these changes, she shared that she is now "more authentic, vulnerable, and feel that I belong more to myself. I am mine."

Now that she's feeling more like herself, Crystal has also changed her social media presence to something that feels more genuine, saying in one post, "I used to be worried about what I posted on social media (even more so in the Playboy days), but now I'm just posting whatever makes me happy instead of curating things for engagement."

When the "Secrets of Playboy" documentary series was released in January 2022, many women who had been involved with Hugh Hefner and the Playboy world came forward with stories of what really went on in the Playboy empire — and most of it is not good.

Although Crystal has defended Hefner in the past, it appears that her relationship with her husband was more complicated than it appeared, and she now has her own stories to tell. In a February 2022 Instagram post, she wrote, "I chose to be more private over the years because I'm an introvert at heart and while the mansion in some ways was a sanctuary, in other ways I was exploited like never before." She continued to explain that she has yet to open up because her story is "complicated and conflicting in ways." However, she believes the only way to tell her story is by being "100% honest and transparent."

Her book will detail "how power, greed, narcissism, and a girl's quest to feel loved, powerful, important, and have a sense of belonging led her down a dangerous path," per her Instagram. While there is currently no set date for when Crystal's memoir will be released, she said that she's teamed with Idea Architects, whom she calls "one of the best literary agencies in the world." She finishes the post by sharing that "the story of my life, being part of Playboy and Hef's world ... is coming soon."