Hugh Hefner

Hefner married Northwestern University student Mildred Williams (1927-) in 1949. They had two children, Christie (born November 8, 1952) and David (born August 30, 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 sleep with other women, out of guilt for her infidelity and in the hopes that it would preserve their marriage. They 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, Brande Roderick, 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. He moved from Chicago to Los Angeles.

Hefner had a minor stroke in 1985 at age 59. After reevaluating 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. The couple had two sons, Marston Glenn (born April 9, 1990) and Cooper Bradford (born September 4, 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, Conrad moved into a house next door to the mansion. According to an update on Hefner's Twitter account on April 25, 2010, Conrad and her mother are moving to Reno in a new home to be closer to family.

Hefner then began to move an ever-changing coterie of young women into the Mansion, even dating up to seven girls at once, among them, Brande Roderick, Izabella St. James, Tina Marie Jordan, Holly Madison, Bridget Marquardt, Rachael O'Neill, and Kendra Wilkinson. The reality television series The Girls Next Door depicted the lives of Madison, Wilkinson and Marquardt at the Playboy Mansion. In October 2008, all three girls made the choice to leave the mansion. Hefner was quick to rebound and soon began dating his new "Number One" girlfriend, Crystal Harris, along with 20-year-old identical twin models Kristina and Karissa Shannon. The relationship with the twins ended in January 2010. After an 11-year separation, Hefner filed for divorce from Conrad stating irreconcilable differences. Hefner has said that he only remained married to her for the sake of his children, and his youngest child had just turned 18. The divorce was finalized in March 2010. On December 24, 2010, Hefner presented an engagement ring to Harris, publicly announcing the proposal the following day. Hefner and Harris plan to marry June 18, 2011.