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Hefner agreed with Morgan that maybe he needed to get his head examined if he was seriously considering getting married for a third time, then at 85 to a 25-year-old woman. The father of four was previously married to Mildred Williams from 1949 until 1957, when he was getting his magazine off the ground, and then took a long bachelor break before marrying Kimberley Conrad, 36 years his junior, in 1989. They separated in 1998 and she moved next door to the Playboy Mansion with their young sons Cooper and Marston, but wouldn’t divorce until 2010.
“I made the commitment, quite frankly, because I felt that I had, in a previous relationship with Holly, not been there for her in a way that she wanted me to be. I just wanted to do whatever would make the relationship work!” Hefner told Morgan. “You know, I was ready to settle down, it was about time.” He smiled. “But on another level I must say, quite frankly, the following Monday, I woke up and I was single and I thought, this is the natural way of things. I ought to be single.”
He explained that he had told Crystal that, if she was having doubts, he was fine calling off the wedding, but he was surprised to find her gone for good just as weekly Sunday Movie Night at the Playboy Mansion had gotten underway. She told him she had gone to stay with her mother in San Diego, but Hef was skeptical, having been unable to reach her there.
“I think an argument could be made that she took me for a ride,” Hefner nodded. “But I must say, quite frankly, it was a pretty nice ride.” Morgan laughed. “It was two and a half very good years and if she was faking it she did it very well.”