Like all promiscuous men, Hefner had his heart broken by his first wife, Mildred, who confessed to having extramarital relations while he was away in the army. In an attempt to compensate, Mildred allowed Hefner to sleep with other women (emphasis on the plural there), which ultimately resulted in their divorce.
The divorce proved timely as Hefner reinvented himself to suit the lifestyle he promoted in Playboy, an instant success after featuring Marilyn Monroe on its cover. As someone who promotes all aspects of the sexual spectrum, it’s not surprising that he has dabbled extensively in both monogamy and polyamory.
Though of course he is most well-known for hosting parties at the coveted real estate that is the Playboy Mansion, Hefner ultimately toned down his antics after having a stroke at age 59. With a more family-friendly approach, his daughter eventually took over the handling of Playboy Mansion affairs–though that didn’t stop Hefner from living the good life with multiple models.
At the moment, Hefner is married to 27 year old model and former Playmate of the Month, Crystal Harris. And so, Hefner has shown us that it is possible to have the best of all worlds–and that youth and beauty are an essential component in a significant other of the female sex.
