Recently, Hugh Hefner was left standing at the proverbial altar by his girlfriend Crystal Harris. We all have this impression that Hefner is an elder with a taste for women young enough to be his grandchildren. Despite this, could this Playboy be a sweet man who gets his heart broken all the time?
In the course of his life, almost every love affair has left Hefner behind. However, does this mean that this is what he will be remembered for after he is buried in his crypt next to Marilyn Monroe?
When Hugh Hefner was still shy
Hefner professed to the New York Times that he did not lose his virginity until he was 22 years old. A shy military husband, while he was on duty, his wife first wife Mildred Williams cheated on him. Her infidelity led to a deal where he was allowed to be unfaithful. The couple was married in 1949 and divorced ten years later.
The wild oats years
It was not until his second marriage was over that Hefner sowed his wild oats. During his 11 years in television, he was lovers with many of the Playmates. Although the sexual revolution was in full effect during his TV career from 1959 to 1970, his Playmate affairs soon turned cold. In 1988, eight of his former lovers filed a $35 million lawsuit against Hefner for palimony.
From the brink of death to the wedding altar
After “A Night at the Playboy Mansion” went off the air in 1970, Hefner moved to LA from Chicago. There, he remained a bachelor until he had a near death experience. After a stroke in 1985, he soon became engaged to Kimberley Conrad. They married in 1989, but, like his first wife, Hefner claimed that she cheated on him. This, he stated, was what led to their separation in 1998. The couple was later divorced in 2010.
Seven girlfriends at once and a set of twins
During his years of separation from Conrad, Hefner kept a wide range of Playmates at the mansion from 1998 to 2010. Among them were Crystal Harris and the 2008 to 2010 relationship with twin models Kristina and Karissa Shannon. As we all know, he asked Harris to be his third wife. Unfortunately, on July 13, Harris called off the wedding five days before it was planned to commence. With that, Hefner was left broken-hearted once again.
A better legacy than reputation as a lover
While Hefner may have made his fortune with Playboy, his real legacy will extend beyond the bedroom. In the non profit world, this legend is well known for giving to charities that support children with autism and animal rescues. He also fights political censorship in the press and regularly hands out the Hugh Hefner First Amendment Award.
In other words, even though Hefner has had a rough time with women throughout his life, he did not let it spoil his positive attitude and generous nature. For these reasons, we could all learn a life lesson from America’s longest reigning Playboy.