After his first divorce in 1959, Hugh Hefner spent several years being “involved with” eleven out of twelve months’ worth of Playmates every year.
The media mogul boasted about it in a 2010 profile with The New Yorker.
Soon after, eight of his ‘Playmates’ filed a palimony suit against him.
“He promised to marry me, he promised to have a child with me, promised to support me,” Leigh, who was the covergirl of Playboy in 1983, said in a press conference, People reports. She was attempting to sue Hefner for $5 million – a move Hefner labelled “silly” because he was “the most confirmed bachelor of the 20th century”.
In 2017, knowing everything we know about Hugh Hefner, who died this week at 91 years old, you can’t argue with that.
But what about his steady relationships? There, we have a different story.
Hefner met his first wife, Mildred Williams, at college at Northwestern University in Illinois.
Williams – like Hefner – was born in 1926 and the pair were married in 1949. They have two children together, Christie (born 1952) and David (1955), and were divorced 10 years after they were married.
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The next, more consistent, woman in Hefner’s life was actress and model Barbi Benton. She and Hefner were (that word again) “involved” from 1969 through to the mid-70s, according to Associated Press as reported by Fox News.
Their relationship began after Benton appeared on Hefner’s television show Playboy After Dark – alongside the man himself. It’s rumoured that, when Hefner asked her out, Benton, then 19, said:
“I’ve never dated anyone over the age of 24”, to which he replied: “That’s okay. Neither have I”.