In Pics: At 86, Playboy boss Hefner to marry 26-Year-Old babe
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Crystal and Hefner were previously engaged in 2011, but called the wedding off at the last minute. Their split was amicable at first, but eventually turned ugly with allegations of infidelity on both sides.
In a classy move, Crystal divulged some intimate and troubling details about her relationship with Hefner to Howard Stern on his radio show, such as that she and Hefner only had sex once and that it lasted “two seconds.
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Hefner has historically dated women much younger than him, and many of them at a time. Hefner married Northwestern University student Mildred Williams (born 1926) in 1949.
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Hefner admitted to being involved with maybe eleven out of twelve months' worth of Playmates" during some of these years.
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Hefner soon switched to an ever-changing coterie of young women into the mansion, even dating up to seven girls at once, among them, Brande Roderick, Izabelloe St James, Tina Marie Jordan, Holly Madison, Bridget Marquardt and Kendra Wilkinson.
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Hefner was once asked about his sex life and the entrepreneur stated that he has slept with 99 out of every hundred playboy playmates. When asked about Pamela Anderson, who herself has been a playboy playmate, Hefner replied that Pamela was in a relationship when she shot for Playboy and he was in a relationship as well. He added that perhaps the timing was not right.
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On December 24, 2010, Hefner presented an engagement ring to Crystal Harris, publicly announcing the proposal the following day. Hefner and Harris had planned to marry June 18, 2011. Harris called off the wedding just 5 days before they were due to be wed. As of June 2012 Harris and Hefner have resumed their relationship, and as of December they are re-engaged, the wedding being scheduled for New years eve.
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In October 2008, all three girls made the choice to leave the mansion. Hefner was quick to rebound and soon began dating his new "Number One" girlfriend, Crystal HaRRIS, along with 20-year-old identical twin models Kristina and Karissa Shannon.