A very detailed Esquire article about Playboy kingpin Hugh Hefner reveals an interesting, yet terrifying statistic. Hefner, who married his third wife, Crystal Harris, on New Year’s Eve 2012, claims he has bedded more than 1,000 women in his life.
When asked for the number of women he’s been with, Hef responds, “How could I possibly know? Over a thousand, I’m sure.” However, he says he’s always been faithful in his marriages. “There were chunks of my life when I was married, and when I was married I never cheated,” he explains, “But I made up for it when I wasn’t married. You have to keep your hand in.”
Hefner has admitted in the past, though, that he slept with other women with the permission of his first wife, Midred Williams. She allowed it after admitting she had cheated on him while he was in the military. They divorced in 1959. Hefner was married to his second wife, 1989 Playboy Playmate of the Year Kimberley Conrad, from 1989 until 2010, though she and Hugh separated after nine years. At age 86, Hefner is a full 60 years older than his current 26-year-old wife, Harris.