Hefner has been married twice. His 1959 breakup of his first marriage to Millie Williams, whom he married in 1949, is believed linked to his commencing his Playboy empire. His daughter Christie, born in 1954, is issue of this marriage. Christie joined her father's editorial staff, and now holds the title of Chairman of Playboy.
He later married Playmate Kimberley Conrad in 1988. Conrad later became Playmate of the Year in 1989. This marriage broke up in 1998. Two sons were issue of this marriage -- Marston, born 1990 and Cooper, born 1991. During this period, Hefner lived monogomously.
He has had a long line of mistresses, including several Playboy Playmates of the Year. These have included Marilyn Cole (PMOY 1971), Lilian Muller (1976), Patty MacGuire (1977) , Terry Welles (1981) and Brande Roderick (2001). The lattermost lived openly with three other blonde mistresses, including two twin sisters. Other noteworthy mistresses who were not Playmates of the Year included Barbi Benton (1968-74); ex-Sunday School teacher Sandra Theodore (1974-81) and Carrie Leigh (1982-86). The lattermost liasion ended with an attempted palimony[?] lawsuit by Leigh against Hefner. There has been no illegitimate issue from any of these couplings.
Hefner, now 77, currently lives with seven blonde mistresses, whose ages range from 18 to 28. He told Vanity Fair magazine "And here's the surprise bit -- it's what they want!"
He purchased the crypt in the Westwood Village Memorial Park Cemetery in Westwood, California beside Marilyn Monroe so as to be interred next to her.
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