Hugh Hefner is living a life that would be a dream of most of the men. A life, that can leave almost anyone jealous.

Hefner's first marriage was with Mildred Williams, from whom he had two children, Christie and David. Mildred had confessed to Hefner about an affair she had prior to their marriage 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. However, they divorced in 1959

After the separation with Mildred, Hefner admitted being "'involved' with some playmates. 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.

Hefner toned down his all-night parties significantly in 1985 after a minor heart attack. In 1989, he married Playmate of the Year Kimberley Conrad. The couple had two sons, Marston Glenn and Cooper Bradford. He and Conrad separated in 1998.

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, and Kendra Wilkinson. For a few years, Kendra Wilkinson, Bridget Marquardt, and Holly Madison were Hugh Hefner's live-in girlfriends, and their relationship was the subject of a hit reality show on E! called "The Girls Next Door". In October 2008, all three girls left the Playboy mansion in Los Angeles where they were living with Hefner. His new "Number One" girlfriend then became Crystal Harris, along with 20-year-old identical twin models Kristina and Karissa Shannon. The relationship with the twins ended in January 2010. Hefner had plans of marrying Crystal on June 18, 2011.

But he was dumped by his fiancée Crystal Harris just five days before their wedding date. She later publicly spoke about their bed room scenes and revealed the reason behind her last minute change of mind on a radio show, claiming that he never turned her on. She also stated that the 85-year-old lasted 'like two seconds' and that he never satisfied her.

The founder of the Playboy Enterprises soon announced the name of the new girlfriend, Shera Bechard who was the Miss November 2010.

Here are a few of the collections of pictures of Hefner and the women in his life.

Shera Bechard
Shera Bechard is seen in this handout image obtained June 28, 2011. Two weeks after Playboy founder Hugh Hefner was dumped by Miss December 2009 just before their wedding, Hefner said on June 27, 2011 that he was now dating Miss November 2010. The 85-year-old magazine mogul moved on to Shera Bechard after Crystal Harris had second thoughts about becoming the third Mrs. Hugh Hefner. Bechard, a 27-year-old French-Canadian model and fledgling actress, moved into the Playboy Mansion in April. REUTERS/Courtesy of Playboy/Ha
Hugh Hefner with Playmates
Hugh Hefner (C), Playboy magazine founder, Playboy Playmates and girlfriends arrive at the American Film Institute's 'AFI Life Achievement Award, A Tribute to Sir Sean Connery' taping in Hollywood June 8, 2006. The show that honored Connery's long career will be telecast on the USA Network cable channel on June 21. REUTERS/Fred Prouser
Playboy magazine founder Hugh Hefner
Playboy magazine founder Hugh Hefner (L) gives a kiss to Miss December '92 Barbara Moore at a reception for newly named 2006 Playmate of the Year Kara Monaco at the Playboy Mansion in Los Angeles, May 4, 2006. REUTERS/Chris Pizzello
Playboy founder Hugh Hefner and his girlfriends
Playboy founder Hugh Hefner and his girlfriends arrive at the E! Entertainment television summer splash party. Playboy founder Hugh Hefner (C) and his three girlfriends Holly Madison (2nd L), Bridget Marquardt (2nd R) and Kendra Wilkinson (R) arrive at the E! Entertainment television summer splash party at the Tropicana bar at the Roosevelt hotel in Hollywood August 1, 2005. REUTERS/Mario Anzuoni
Playboy founder Hugh Hefner 2nd L, surrounded by his three girlfriends
Playboy founder Hugh Hefner (2nd L), surrounded by his three girlfriends Holly Madison (L), Bridget Marquardt (2nd R) and Kendra Wilkinson, laughs as he addresses questions at the panel for E! networks television show "The Girls Next Door" at the Television Critic's Association Summer press tour at the Beverly Hilton Hotel in Beverly Hills July 17, 2005. The eight episode reality series takes viewers beyond the gates of Hefner's Playboy mansion. REUTERS/Mario Anzuoni MA/JJ
Hugh Hefners Planking Playmates in Pictures
Playboy magazine founder Hugh Hefner (C) arrives with friends for an ESPY Awards pre-party at the Playboy Mansion in Beverly Hills, California, July 12, 2005. Hefner is joined by Kendra Wilkinson (L), Bridget Marquardt (2nd L) and Holly Madison. The 13th Annual ESPY Awards gather participants in the sports and entertainment worlds to celebrate the best performances of the past year. The Awards will be held on Wednesday at the Kodak Theatre. REUTERS/Robert Galbraith RG/PN
Hugh Hefner and his fiancee, Playboy Playmate Crystal Harris
Hugh Hefner and his fiancee, Playboy Playmate Crystal Harris, arrive at the opening night gala of the 2011 TCM Classic Film Festival featuring a screening of a restoration of 'An American In Paris' in Hollywood, California April 28, 2011. REUTERS/Fred Prouser
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