Hugh Hefner's Many Exes

Mildred Williams
It’s hard to imagine Hef with someone his own age, but long before he was a media mogul, Hef married fellow 23-year-old Mildred Williams in 1949. The couple went on to have two children – daughter Christie, now 60, and son David, now 57 – before divorcing in 1959. Christie would grow up to become chairwoman and CEO of Playboy Enterprises.

Mildred Williams
It’s hard to imagine Hef with someone his own age, but long before he was a media mogul, Hef married fellow 23-year-old Mildred Williams in 1949. The couple went on to have two children – daughter Christie, now 60, and son David, now 57 – before divorcing in 1959. Christie would grow up to become chairwoman and CEO of Playboy Enterprises.