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Crystal Harris called off her engagement to Hugh Hefner days before their wedding, the two confirmed on June 14, 2011. The Playboy mogul said on his Twitter page that she left him and took her dog Charlie with her.
Also on June 14, 2011, Harri's debut single, 'Club Queen,' was released online.
Harris and Hefner became engaged in December 2010 - when he was 84 and she was 24 - and have been linked together for about two years. Hefner has dated many Playboy Playmates and has lived with small groups of them at a time in his home.
Harris appeared on the E! reality show, 'The Girls Next Door,' which showcased the lives of Hefner's girlfriends at the Playboy mansion and once starred ex-girlfriends Holly Madison and Kendra Wilkinson.
Hefner has been married twice. He and Playboy Playmate Kimberley Conrad wed in 1989 and divorced in March 2010. They have two sons - Marston and Cooper.
Hefner and his first wife, Mildred Williams, were married between 1949 and 1959 and are parents to Christie and David.
(Pictured: Hugh Hefner and Crystal Harris appear in a photo posted on his Twitter page in December 2010.)