In 1949, Hefner married Northwestern University student Mildred (“Millie”) Williams, who was also born in 1926. They had two children: daughter Christie Hefner (born 1952) and son David (born 1955). Before the wedding, Mildred confessed that she had an affair while he was away in the army. He called the admission “the most devastating moment of my life.” A 2006 E! True Hollywood Story profile of Hefner revealed that Mildred allowed him to have sex with other women, out of guilt for her infidelity and in the fond hope that it would preserve their marriage. The two were divorced in 1959.
Hefner remade himself as a bon vivant and man about town, a lifestyle he promoted in his magazine and two TV shows he hosted, Playboy’s Penthouse (1959–1960) and Playboy After Dark (1969–1970). He admitted to being “‘involved’ with maybe eleven out of twelve months’ worth of Playmates” during some of these years. Donna Michelle, Marilyn Cole, Lillian Müller, Shannon Tweed, Barbi Benton, Karen Christy, Sondra Theodore, and Carrie Leigh — who filed a $35 million palimony suit against him — were a few of his many lovers. In 1971, he acknowledged that he experimented in bisexuality. Also in 1971, Hefner established a second residence in Los Angeles with the acquisition of Playboy Mansion West and, in 1975, moved there permanently from Chicago.
Hefner had a minor stroke in 1985 at the age of 59. After re-evaluating his lifestyle, he made several changes. The wild, all-night parties were toned down significantly and in 1988, daughter Christie began to run the Playboy empire. The following year, he married Playmate of the Year Kimberley Conrad; they were thirty-six years apart in age. The couple had two sons: Marston Glenn (born 1990) and Cooper Bradford (born 1991).The E! True Hollywood Story profile noted that the notorious Playboy Mansion had been transformed into a family-friendly homestead. After he and Conrad separated in 1998, she moved into a house next door to the mansion.
In January 2009, Hefner started dating Crystal Harris, joining the Shannon Twins after his previous “number one girlfriend”, Holly Madison, had ended their 7-year relationship. On December 24, 2010, he became engaged to Harris, to become his third wife. Harris broke off their engagement on June 14, 2011, five days before their planned wedding. In anticipation of the wedding, the July issue of Playboy, which reached store shelves and customer’s homes within days of the wedding date, featured Harris on the cover and in a photo spread as well. The headline on the cover read “Introducing America’s Princess, Mrs. Crystal Hefner”.
Hefner’s brother Keith died at the age of 87 on April 8, 2016, one day before Hefner’s 90th birthday.
Hefner died at his home in Holmby Hills, Los Angeles, California on September 27, 2017, at the age of 91
Credit for photo: shemazing.ie