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Hefner was first married in 1949 to a Northwestern University student named Mildred Williams, with whom he has two children ― Christie and David ― before divorcing in 1959.
In 1989, he married again, this time to Playmate of the Year Kimberley Conrad, who was 36 years his junior. Together the couple had two sons, Marston and Cooper, before they separated in 1998 and divorced in 2010.
Hugh Hefner, Marsden Hefner and wife Kimberly Conrad at the Playboy Playmate of the Year Celebration on April 25, 1991. (Ron Galella via Getty Images)
During his 12-year separation from Conrad, Hefner had relationships with many of the young models featured in his magazine, including twin sisters Sandy and Mandy Bentley, and even dated seven women at once. His concurrent relationships with Playboy Playmates Holly Madison, Bridget Marquardt and Kendra Wilkinson were featured on the reality series "The Girls Next Door."
In 2008, all three women decided to leave Hefner and the Playboy Mansion, prompting Hefner to start dating Crystal Harris, who was 60 years his junior, along with 20-year-old twins Kristina and Karissa Shannon. Hefner broke things off with the twins and proposed to Harris in 2010.
The couple planned to marry in June 2011, but Harris decided to call off their nuptials just five days before they were scheduled to exchange their vows. After some highly publicized fighting over the custody of their dog, the couple reconciled with the help of Hefner's longtime secretary Mary O'Connor, who died in 2013. Hefner said "I do" to Harris and tied the knot for a third time on Dec. 31, 2012.
CORRECTION: An earlier version of this obituary included a photo caption that misspelled the surnames of Marlon Brando and Hugh Hefner.
This article originally appeared on HuffPost.
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