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Before their wedding, Mildred told Hefner that she had had an affair; he has called the admission "the most devastating moment of 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."<3> 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 palimony 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.<4>
On July 1, 1989, he ended a 30-year run as a bachelor and married Kimberley Conrad, that year's 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. Hefner soon selected 27-year-old Yazmin King as favorite. Later, Tina Marie Jordan became Hefner's "primary" girlfriend, and he quickly selected more young blondes for a posse of 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. Hefner celebrating his 80th birthday with Kendra and Bridget in Munich, April 2006. Hefner celebrating his 80th birthday with Kendra and Bridget in Munich, April 2006.
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.
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