There is absolutely no way to keep track of all the women ‘Hef’ has been with. He doesn’t even know the exact number, but claims that he’s definitely been with over a thousand women, in the biblical sense anyway. Not even Hugh Hefner would have been able to actually date all of them. So, we decided to stick with those that he actually married.
The first time he walked down the aisle was in 1949. That was with college sweetheart Mildred Williams. He married her even though she had confessed to cheating on him while he was away during WWII. Apparently Hugh called it the “most devastating moment of my life”. Whilst they did marry, Mildred allowed Hugh to sleep with other women in an effort to make up for the guilt she felt for cheating on him to begin with.
It seems, however, that that only served to whet his appetite and the two got divorced in 1959. They did have two children, however.
After the divorce Hugh not only founded his now world-famous Playboy, but he also started to surround himself with young, pretty women. It became his signature mark. Rarely was he ever seen without a gaggle of women following him around and fawning over him. Back then he was still a reasonably good looking guy and he soon made a fortune with his magazine as well, which made him a very eligible bachelor.
It took him another 30 years, however, before he married again. In 1989 he married Playmate of the Year Kimberly Conrad. With her he had two sons.
Hugh had suffered from a minor stroke in 1985, which had prompted him to make some lifestyle changes. He’d been 59 at the time and he stopped partying all night and his daughter took over as Playboy CEO. Once he was married again and had two young children, he even transformed the Playboy Mansion into a family friendly home.
However, after 9 years the couple separated and Kimberly moved into a house next door, so that the boys could stay close to their father. It was for them that the estranged spouses decided not to get a divorce. It’s a curious thing, however. Hugh had short-lived affairs with any number of Playboy Bunnies and long-term relationships with some women as well. Whilst he was certainly a father to his sons, he was definitely not a husband to his wife. There seems little point to stay married, but Hugh had no desire to get married again either, so it probably didn’t make much of a difference.
Hugh had agreed that he would pay $250,000 in alimony to Kimberly, which he dutifully did. When she decided to sue him for $5 million over the sale of a home that the couple owned together, Hugh seemed to have had enough and filed for divorce. That was in September 2009.
He didn’t think that he owed Kimberly any money and since she decided to become greedy, it was time to sever ties. The divorce was finalized in 2010.
By that time he was already dating Crystal Harris. After his divorce, at age 84, he once more wanted to get married and in December 2010 Hugh and Crystal were engaged. Alas, six months later when the wedding was set to take place, Crystal got cold feet and did a runner. That was only 5 days before their actually wedding and the new Playboy magazine had already been printed, touting her as the new Mrs. Hefner on the front page. Instead of cancelling the issue, they merely put a sticker that read “Runaway Bride” to cover her face.
But that wasn’t the end of the story. Somehow Crystal managed to warm her feet up again and she and Hugh reconciled. Feeling more confident the second time around, she eventually married Hugh, who is 60 years older than her, on New Year’s Eve 2012.
Needless to say that it only took until 2013 for the first divorce rumours to appear. They were quickly denied and Crystal went public saying that she married Hugh for security reasons. Whilst she would never be part of his last will, the ironclad prenuptial agreement would see it that she would be taken care of. Crystal did make sure to profess her genuine interest in and love for Hugh, though. She says he is very smart and she learned so much from him and they can always talk about anything. But she declined to comment on their marital relations, which is quite understandable. Everyone might be more curious than is decent, but it is a private matter.
Hugh himself said that he can’t see himself being with anyone else any more. He doesn’t want to get a divorce and believes he will stay married to Crystal until his dying day. He is 90 years old now, so he has no illusions about his remaining lifespan. Crystal seems content with that.
Of course, on their 3rd wedding anniversary eyebrows were raised because neither Crystal nor Hugh made any mention of the fact on social media nor did they mention each other in any way. It’s been speculated that the conspicuous absence of any pictures of the two of them together on each of their social media accounts means that the two are headed for divorce.
Thus far that has not happened and we can’t imagine that Hugh really wants to go through another divorce at his age.