The late Hugh Hefner was nearly as famous for his love life as he was for founding the groundbreaking Playboy enterprise. After first publishing the men’s entertainment magazine in 1953, he would go on to open clubs, casinos and hotels with the iconic name and logo — but the women on his arm were always just as newsworthy.
From dating models to actresses to his very own Playboy centerfolds, Hugh was soon recognized for having multiple live-in girlfriends at the Playboy Mansion. Perhaps the most famous of these paramours were the stars of the reality show Girls Next Door: Holly Madison, Bridget Marquardt and Kendra Wilkinson. Hugh never married any of these women, though.
Despite having three marriages, Hugh’s wives were not always happy being with the Playboy mogul. His third wife, Crystal Hefner, revealed in an interview in January 2024 that she was never “in love” with Hugh.
Keep reading to find out all there is to know about the only three women who got Hugh to put a ring on their finger!
Hugh met his college sweetheart, Mildred Williams, at Northwestern University. The pair remained a couple while Hugh served in the army from 1944 to 1946, according to Insider. When he returned home, Mildred admitted to Hugh she had carried on an affair while he was away at war. “I had literally saved myself for my wife, but after we had sex she told me that she’d had an affair,” Hugh told Daily Mail in 2007. “That was the most devastating moment in my life.”
Despite the infidelity, Hugh and Mildred married anyway in 1949. In Hugh’s E! True Hollywood Story from 2006, it was claimed that Mildred allowed Hugh to have sex with other women during their marriage to lessen her guilt. The pair would welcome daughter Christie in 1952 and son David in 1955. Christie would go on to be the Playboy Enterprises Chairman and CEO for 20 years until she stepped down in 2008. After a decade together, Hugh and Mildred split in 1959.
After dating several high-profile women for a few decades, Hugh decided to settle down once again with 1989’s Playmate of the Year Kimberly Conrad. Although there was a 36-year age difference between the two, the couple married in 1989 and welcomed son Marston in 1990 and son Cooper in 1991. The union reportedly made the Playboy Mansion a more family-friendly environment.
Hugh and Kimberly separated in 1998 but didn’t officially divorce until 11 years later in 2010, as Kimberly remained focused on co-parenting. “I would’ve been happy to divorce her when we separated, but she wanted to remain married for our boys,” Hugh told People in 2009. In 2017 at the age of 55, Kimberly recreated her Playboy cover alongside other notable vets.
In January 2019, Hugh began dating Crystal Harris after Holly called it quits as his “number one girlfriend.” Hugh proposed to Crystal in 2010. However, in June 2011, just five days before their wedding, she ended the engagement. After reconciling, they married on New Year’s Eve in 2012. “Crystal and I married on New Year’s Eve in the Mansion with [younger brother] Keith as my Best Man,” Hefner tweeted the day of the wedding. “Love that girl!”
Although there were skeptics of Crystal’s intentions considering the 60-year age gap, the former model remained by Hugh’s side as his health was failing. When he died in September 2017 at the age of 91, Crystal was reportedly completely devastated by the news. “I am heartbroken. I am still in disbelief,” she said in a statement at the time. “He is in the place he was always certain he wanted to spend eternity. He was an American hero. A pioneer. A kind and humble soul who opened his life and home to the world.”
Crystal talks about her marriage to Hugh in her memoir Only Say Good Things: Surviving Playboy and Finding Myself, out January 23, 2024. In an interview with PEOPLE, she said she was never “in love” with the late star, and that she eventually “realized I was dealing with a really big power imbalance” with the late star. “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,” she added.