Hugh Hefner’s Wives: World’s Most Famous Playboy’s Wives Cheated On Him

Hugh Hefner died Wednesday at the age of 91, and the ubiquitous image of him flanked by playmates can sometimes obscure the fact that the Playboy founder had made quite a few attempts at marriage.

Hefner was married three times, and in spite of being known for sleeping with “more than 1000 women,” the real-life playboy admitted he never cheated on any his wives.

"There were chunks of my life when I was married, and when I was married I never cheated," Hefner said, Mail Online reported. "But I made up for it when I wasn't married. You have to keep your hand in."

But the same cannot be said for the women he was married to, and all of them reportedly cheated on him. Here is a look at Hefner’s multiple attempts at having a successful marriage:

Mildred Williams

Williams fell in love with Hefner at a party after high school. Even though the Playboy mogul had to leave as he was deployed in the Army, they kept the flame alive by writing letters to each other. However, Williams ended up cheating on Hefner with another man, an affair about which she opened up to him.

Despite the confessions of infidelity, Hefner decided not to hold it against her and both of them exchanged vows on June 25, 1949. Together they had two children – Christie and David. The couple divorced in 1959, after 10 years of marriage, EzineMark reported.

Kimberley Conrad

Conrad was a model and actress who rose to prominence after she began a romantic relationship with Hefner. After she became the “Playmate of the Year” in 1989, she got married to Hefner. Both of them had two children – Marston and Cooper – before they separated after nine years of marriage, the Famous People reported.

However, Hefner officially filed for divorce from Conrad in 2010, revealing that she had cheated on him during their marriage. “I am happy to be out of the marriage. I only remained married for the sake of the children, at her request.” Hefner said, Mail Online reported.

Crystal Harris

Following his separation from Conrad, Hefner moved in with Harris in his Playboy Mansion along with the famous blonde twins — Karissa and Kristina Shannon. They got married on New Year’s Eve 2012, at the Playboy Mansion, the only marriage of Hefner that did not end in a divorce.

However, the marriage was not smooth-sailing as people thought. A previous attempt to get hitched in 2011 had ended up in farce as the Playmate of the month infamously ran from the altar, reportedly because she got cold feet.

Then she went on Howard Stern and revealed that sex with Hefner lasted for “like two seconds,” a comment that her the-then ex-fiancé took offence to.

“Crystal lied about our relationship on Howard Stern but I don’t know why,” Hefner tweeted, according to People. “Maybe a new boyfriend?” Replying to another Twitter user’s comment, Hefner wrote: “Crystal convinced me that she adored me. That was the first lie.”

After their marriage, Harris revealed that she had married Hefner because, “it meant more security, knowing that I am the one for him.”

“Like we were talking about, there are always girls in and out and always the feeling of maybe being replaced... And he made sure I didn't feel that way anymore and that was what the wedding was all about,” she added, Mail Online reported.

Hefner’s life did change after he married Harris. Even though he was surrounded by beauties day and night at his mansion, Hefner was no longer the playboy that he once had a reputation to be.

Carla Howe, one of the many blondes who occupied the mansion, told Mirror: “To be honest, he’s so old now I couldn’t imagine him trying to make a move. He has to walk with people around him because he’s frail… The only woman that sleeps with him now is Crystal.”