After this heartbreak, Hugh Hefner married three times and lived up to his playboy reputation till his death.
Our past may not always determine our future actions but in one way or the other, it leaves behind an emotional scar. Playboy tycoon Hugh Hefner had a lifestyle that was incomparable to any other. Surrounded by beautiful and glamourous women for most of his life, Hefner was envied by at least a few.
However, Hefner's life did not begin the way it ended. Years before he built the Playboy empire, Hefner was a one-woman man. Unfortunately, Hefner's loyalty was disregarded by the woman he first loved even before they got married.
Hefner was so in love with his childhood sweetheart Mildred ‘Millie’ Williams that he saved himself for her. They were all set to get married and Hefner looked forward to being with his lady love. “Williams met Hugh shortly аftеr high school аt a party, аnd thе couple wеrе completely smitten. Whіlе ѕhе attended thе University οf Illinois, Hefner deployed wіth thе Army. Thе couple kept іn touch through lіkе letters...," stated Heavy.
However, he never suspected his partner to be keeping a secret from him. Just days before tying the knot, Williams told Hefner that she had an affair while he was away serving in the US military during the Second World War, according to Independent.
"I think the relationship was probably held together by two years of foreplay. That wasn't unusual for our time. In fact, most of my immediate friends didn't have sex until they married. Milly and I had it just before," recalled Hefner, according to The Sun.
He added, "I had literally saved myself for my wife, but after we had sex she told me that she'd had an affair. That was the most devastating moment in my life." Hefner continued, "My wife was more sexually experienced than I was. After that, I always felt in a sense that the other guy was in bed with us, too."
Though Hefner was heartbroken, he loved his woman dearly. He did not allow her affair to influence his decision to marry her. So in 1949, Chicago-born Hefner married Williams whom he met in college in the mid-40s. The couple went on to have two children, daughter Christie Hefner and their son David. Meanwhile, Hefner was in the middle of building and expanding his brand. With a start-up loan of approx $7700, Hefner founded Playboy.
However, his increasing wealth and fame did not help in making his marriage any successful. Betrayal loomed over his marriage and Hefner slept around with other women with the permission of his wife. After 10 years of being with each other, Hefner and Williams decided to part ways.
With the unbelievable success of Playboy and his divorce, Hefner began to enjoy a hedonistic lifestyle. He hosted extravagant parties at the Playboy Mansion and walked around with famous and high profile women. All eyes were on him and for years, Hefner lived up to his serial ladies man reputation.
In 1989, Hefner finally decided to marry. He exchanged vows with a much younger Kimberley Conrad. The woman was 26 years younger than him. They eventually went on to have two sons.
Despite being in a marriage, Hefner continued his previous lifestyle and kept multiple girlfriends. Soon, the couple separated. However, they officially divorced years later. Conrad, along with her two sons moved out of the Playboy Mansion to a house next door. 20 years later, Hefner and Conrad decided to get a legal divorce. "I would’ve been happy to divorce her when we separated, but she wanted to remain married for our boys," said Hefner to People in 2009.
Hefner lived the absolute bachelor lifestyle, by dating and living with numerous women. He married one last time in December 2010 to 24-year-old Harris before he passed away in 2012, according to Insider.