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Because Hef has never been a one-woman man, there's a lot of overlap.

Hugh Marston Hefner (born April 9, 1926) is an American men's lifestyle magazine publisher, businessman, and a well-known playboy.

At the time, it was more money than I'd ever know what to do with… I actually pitied him for stooping to that level," she wrote in an excerpt quoted by Us Weekly.But luckily for Hef, either Karissa or Kristina has a small mark on her neck that helps him crack the bombshell code. Or is the world's most legendary bachelor just getting that old?Maybe it's the age difference; we know we can't always tell friends' babies apart, and there's a much shorter time span between us and newborns and Hef and his babes.that she was so miserable while she lived in the mansion that she attempted suicide.In the book, out June 23, Holly explains that dating the Playboy mogul "a man who was old enough to be my grandfather," drove her to despair.'s executive features editor Stephen Galloway discovered during his time at the Playboy Mansion, sometimes the dissonance can be shocking.