Answer
The answer is three times. Hugh Hefner, the renowned founder of Playboy magazine, ventured into matrimony on three separate occasions. His first marriage was to Mildred Williams, which lasted from 1949 to 1959. His second union was with Kimberley Conrad, with whom he shared his life from 1989 to 2010. Finally, he exchanged vows with Crystal Harris, their marriage enduring from 2012 until his passing in 2017.