It was after she had an affair that he thought about branching out sexually, and boy did he.
But five days before the wedding, Crystal got cold feet and ended their engagement.
At its peak, it had over seven million subscribers.
Hef asked her to be his number-one girlfriend and move in with him at the Mansion — and to top it off, he asked her to be Miss December 2009.
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One of those sons now runs the magazine and was responsible for temporarily removing nudity.