Before their wedding, Mildred told Hefner that she had had an affair; he has called the admission "the most devastating moment of [his] life." A 2006
E! THS profile of Hefner revealed she allowed him to cheat on her, out of guilt for her infidelity and the hopes that it would preserve their failing marriage.
After his first marriage, Hefner became the world's most famous and envied
womanizer. He has said that during some years, he was "'involved' with maybe eleven out of twelve months worth of Playmates."
Hefner has had sustained relationships with
Donna Michelle, Marilyn Cole, Lillian Muller, Patti McGuire, Shannon Tweed, and
Brande Roderick, all of whom were chosen "
Playmate of the Year." Others include
Barbi Benton, Karen Christy, ex-Sunday school teacher
Sondra Theodore, and actress
Carrie Leigh, who filed a $35 million
alimony suit against him. Benton, who dated him for 8 years, remains a fixture in Hefner's life and a regular visitor to the
Playboy Mansion, which she found for him. In 1971, Hefner has acknowledged, he experimented in bisexuality.
On
July 1, 1989, he ended a 30-year run as a
bachelor and married
Kimberley Conrad, that year's
Playboy Playmate of the Year. They separated in
1999, though have yet to
divorce.
Hefner has 4 children:
Christie Hefner (born
November 8, 1952) and
David Hefner (born
August 30, 1955) with
Mildred Williams, and
Marston Hefner (born
9 April, 1990) and
Cooper Hefner (born
4 September, 1991) with
Kimberley Conrad.
After his separation from Conrad, Hefner began living with an ever-changing coterie of women, ranging in age from 18 to 28. He told
Vanity Fair: "And here's the surprise bit—it's what
they want!" Soon, Hefner assembled another coterie of girlfriends, notably
Brande Roderick. In
2000 she left to take a role in popular series
Baywatch. Later,
Tina Marie Jordan became Hefner's "primary" girlfriend, and he quickly selected more young blondes for a changing posse of usually seven, one of whom was
Holly Madison who joined in
2001. Shortly after
Playboy's 50th anniversary, five of the girlfriends, including
Izabella St. James, left, leaving Holly and
Bridget Marquardt to tend to Hefner.
In 2004
Kendra Wilkinson (also blonde, aged 18) was asked to move into the Mansion to become girlfriend number 3. The 2005-06 E!
reality television series
The Girls Next Door follows these three girlfriends,
Holly Madison, Bridget Marquardt and
Kendra Wilkinson in their life with Hef around the Mansion and on travel.
An
urban legend persists about Hefner and the
Playmate of the Month related to markings on the front covers of the magazine. From 1955 to 1979 (except for a six month gap in 1976), the "P" in
Playboy had a number of stars printed in or around the letter. The legend claims that this was either a rating that Hefner gave to the Playmate according to how attractive she was, the number of times that Hefner had slept with her, or how good she was in bed. Another rumor was that if the stars were inside the "P", Hefner had slept with the Playmate, while if they were outside, he didn't sleep with her. In reality, the stars, which ranged in number between zero and twelve, were solely used to indicate the domestic or international advertising region for that particular printing.
Hefner has donated millions of dollars to the
University of Southern California's School of Cinematic Arts. In 1992, he gave USC $100,000 to create a course, Censorship in Cinema; in 1995 he donated $1.5 million to endow the Hugh M. Hefner Chair for the Study of American Film; and in 2007 he donated $2 million for a central exhibition space in the school's new headquarters complex.