Hugh got hitched for the first time in 1949 to someone with the name of Mildred. That's so long ago, they don't even make girls with that name anymore. He was Midwestern husband for about a decade then his idea for Playboy magazine hit. Once he started making money and was surrounded by women who would do whatever he asked them to in order to get some of that money, his marriage vows seemed as outdated as Mildred's name. There's an old saying of "pimping ain't easy...on a pimp's marriage". A lot of people forget that last part. Hef lived the single life for about 25 more years. Then he decided to marry Kimberly Conrad in 1989. When asked why settle down the old romantic gushed "she's the sweetest piece of a-- in the world". Sadly even the sweetest piece of that will sour over time, and in 1998 Kimberly was asked to move with their 2 kids. Hef was 72 and had more wild oats to sow. He was also reduced to eating Quaker Oats for most of his meals. Hef went through women like most men his age went through Werther's originals.
Then last year at age 85 he proposed again to 24 year old Crystal Harris. But 5 days before the ceremony she ran off with Dr Phil's son, the much more age appropriate Jordan McGraw. Perhaps at 25 he was too immature for the sophisticated Crystal because she ran back to Hugh this Summer. And now they are getting married (as TMZ reports "for reals"). Crystal is playing a dangerous game like they play on game shows. You know the one where the bomb is ticking but it's spitting out money. You have to press stop before it blows up. The longer you wait the more money you get. Except for her it's the longer you wait the less time you have to spend with him. She knocked 18 months off her time, and figured that's about long as she can hold out before his heart may explode.