Playboy's Hugh Hefner engaged to 24-year-old former playmate
December 26th, 2010
08:48 AM ET

Playboy's Hugh Hefner engaged to 24-year-old former playmate

Who says May-Miss December romances don't work?

Hugh Hefner, the 84-year-old Viagra-popping founder of Playboy, is tying the knot for the third time.

This time the lucky gal is 24-year-old Crystal Harris, December 2009 playmate of the month.

“When I gave Crystal the ring, she burst into tears,” Hefner posted on his Twitter account. "This is the happiest Christmas weekend in memory."

“Yes, the ring I gave Crystal is an engagement ring," he clarified later for those asking if it was merely a Christmas present or a step forward for the couple.

Hefner posted that he and Harris spent the night before Christmas watching a movie, then exchanging gifts. Hefner had a few for his girlfriend, which Harris tweeted pictures of, including the legendary diamond Playboy watch.

His big gift was the engagement ring. It was a "memorable Christmas Eve together," Hefner tweeted.

Video: The world's ultimate playboy gets engaged

Hefner's love life has, of course, been well documented including the popular reality show showcasing a trio of girlfriends in "The Girls Next Door."

Hefner and his previous wife, 1988 playmate of the year Kimberley Conrad, were married in 1989 and separated in 1998. They divorced this year. Now Hefner will walk down the aisle half a century after his first marriage in 1959 to Mildred Williams.

But if you think Hef might not be the exact icon of monogamy or a perfect relationship, he begs to differ. In an interview with RadarOnline.com after the breakup of Sandra Bullock and Jesse James, he said more than anyone, he knows all of the sides to a relationship and what makes one work.

"I was married and completely faithful for eight years," he told Radar. "I lived a single life, a playboy lifestyle, before and after it, but while I was married I was faithful to it."  Hefner told the New York Times magazine in July that he uses Viagra which he called "God's little helper" a couple of times a week.

soundoff (1,615 Responses)
  1. The_Mick

    "May-December romance"??? More like May-Money romance! It reminds me of a few bars in Baltimore where half of the women should have "HH" tattoed on their foreheads (Husband Hunter) and the best pickup line is, "I'm single, have a job, and own a house."

    December 26, 2010 at 4:57 pm | Report abuse |
  2. Johnny

    I say, good for him. But for her, I have to say...what does your father think??

    December 26, 2010 at 5:00 pm | Report abuse |
    • Neal

      I bet she's from a single mother family – lots of these now-a-days, and she's therefore looking for a father figure – one who can provides.

      December 26, 2010 at 5:06 pm | Report abuse |
    • brigitte

      My bet is she was abused by some older family member as a child.

      December 26, 2010 at 5:36 pm | Report abuse |
    • kjo

      My guess is, she's had a miserable life and in her perspective, being the wife of some gross old dude is better than her alternative. (Playboy bunnies don't exactly go on to have bright and happy futures)

      December 26, 2010 at 6:08 pm | Report abuse |
    • kjo

      who cares what her dad thinks? her dad isn't the one who has to wake up to hugh hefner's face every day. *GAG*

      December 26, 2010 at 6:14 pm | Report abuse |
  3. Anita

    I wonder if a man would be considered "lucky" if he were marrying a woman 60 years older than he was.

    December 26, 2010 at 5:02 pm | Report abuse |
    • Neal

      Totally unlucky. That woman's family would ensure he gets no money in case of a divorce. Not only that, there would probably be some kind of abuse charges against him so he won't even see his step children.

      December 26, 2010 at 5:05 pm | Report abuse |
  4. Neal

    Our "woman who brings nothing into a marriage still can leave a marriage with bags of cash" social arrangement ensures these type of things will keep happening – young girls old guys, old women dumped for young girls, etc..

    December 26, 2010 at 5:03 pm | Report abuse |
  5. Jo An

    $$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$Oh Well!!! Economy is bad!!

    December 26, 2010 at 5:08 pm | Report abuse |
  6. Fred Davis

    What a sherade. Pokes fun at marriage. But it's not for the money, is it?!!

    December 26, 2010 at 5:08 pm | Report abuse |
  7. Skull

    He has looked foolish for decades but can afford to. It's more disgusting and shameful these girls that do this over and over.

    December 26, 2010 at 5:09 pm | Report abuse |
  8. Rob

    Omg!!!! All about the mulah... What do you think is the life expectancy of Hef? You do the math.. She hasn't lived long enough to know about life let alone Hef... I know she's a ditz!!!

    December 26, 2010 at 5:11 pm | Report abuse |
  9. Dorre Day

    ewe...gross

    December 26, 2010 at 5:13 pm | Report abuse |
  10. Terry

    When he was 50 or 60 and doing 20 yr olds I thought well ok for him but now it's just EWWWW I've heard of Daddy and Granddaddy complexes before but never Great-Great Granddaddy.

    December 26, 2010 at 5:13 pm | Report abuse |
  11. Jim K.

    Who are we to judge? "Let he who is without sin cast the first stone." Merry Christmas and Happy Holidays everyone... and congratulations Hef and Crystal.

    December 26, 2010 at 5:17 pm | Report abuse |
  12. taffd

    What brainless bimbo whose only assets are boobs and a hoo-haw doesn't love a mega-rich old geezer supercharged with viagra. I'm sure she's thinking"he can't last forever." tee hee giggle giggle

    December 26, 2010 at 5:19 pm | Report abuse |
    • Carmen

      By your description that wouldn't make her brainless as much as shrewd.

      December 26, 2010 at 5:46 pm | Report abuse |
  13. evensteven

    . . . pink and wrinkly . . .

    December 26, 2010 at 5:19 pm | Report abuse |
  14. Palms

    I wonder what the two families think of this union?

    December 26, 2010 at 5:21 pm | Report abuse |
  15. Bradley L.

    LOL.... all you guys talking about gold diggers makes me laugh.. I mean these are playboy playmates for freaking sakes!!! of course they're gold diggers!!!! Maybe I'm naive BUT I've never seen any gal who posed for playboy so she could be the next mother theresa or because she wanted to help poor children in 3rd world countries!!!!!

    December 26, 2010 at 5:21 pm | Report abuse |
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