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 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. DP

    This marriage union looks good on her resume!

    December 26, 2010 at 6:38 pm | Report abuse |
  2. pdikeman

    I see...said the blind man......

    December 26, 2010 at 6:38 pm | Report abuse |
  3. cynthia

    Hugh Hefner has become a parody of the playboy persona that he has always cultivated. He cannot seriously think that a 24 year old woman could be in love with an 84 year old man - at least romantically. Even the most delusional person could look at this situation and know that the woman is in it for the money. Hugh just looks pathetic.

    December 26, 2010 at 6:46 pm | Report abuse |
  4. disappointed


    December 26, 2010 at 6:47 pm | Report abuse |
  5. Amy

    Eww, gross!

    December 26, 2010 at 6:51 pm | Report abuse |
  6. MartyT

    Oh well... if she dies, she dies.... Good luck Hef!

    December 26, 2010 at 6:54 pm | Report abuse |
    • Indiana-Gene

      MartyT,,, Now that is FUNNY!

      December 26, 2010 at 7:57 pm | Report abuse |
  7. Eva

    Gross. That chick looks like a man.

    December 26, 2010 at 6:57 pm | Report abuse |
    • frontgate

      ha, ha, ha, yeah, right.

      December 26, 2010 at 6:58 pm | Report abuse |
    • Bill Clinton

      oh, ooo. Yucky! I feel his pain.

      December 26, 2010 at 7:16 pm | Report abuse |
    • Dude

      Hahaha Eva and what do you look like..!!!

      December 26, 2010 at 7:21 pm | Report abuse |
    • Porchiaknows

      No Eva, that IS a man on the left. A dirty old man and a bimbo chick.

      December 26, 2010 at 7:29 pm | Report abuse |

      I'm suprised you can type with paws.

      December 26, 2010 at 7:30 pm | Report abuse |
    • Gerry0625

      A man really, your just sad cause on your best day this 80 something year old man still get amazing looking women! looks might not be everything but they help.

      December 26, 2010 at 7:34 pm | Report abuse |
    • Mike Schumer

      Someone said the same thing about Fran Townsend. I don't get it. Both these women look very much like women and damn good looking ones at that.

      December 26, 2010 at 8:56 pm | Report abuse |
    • Picapollo

      and the man looks like a raisin 😛

      December 26, 2010 at 9:10 pm | Report abuse |
    • groovygoober

      Lol, no gerry0625, it is not that man getting the chicks, it's his money.

      December 27, 2010 at 2:38 pm | Report abuse |
    • Babak from LA

      I am not gay but if that looks like man, I am switching batters!!!!

      December 27, 2010 at 7:01 pm | Report abuse |
  8. Kay

    Good for him 🙂 he will get it tell he dies! YOU boys are just jealous! Lol

    December 26, 2010 at 6:57 pm | Report abuse |
  9. mahdeealoo

    Really cool to know half the men in the world have seen your fiance' naked. ew

    December 26, 2010 at 7:01 pm | Report abuse |
    • Scarf

      Looking at naked girls in Playboy used to be fun but then I turned 13 by which time it was "old hat".

      Good for ol Hef I guess but hardly a "soul mate".

      I used to joke in college that most women fit into one of three categories; drug sniffers, jock sniffers and wallet sniffers. Guess which one this girl definitely is. In time the tables will turn and she will be a widow with a wallet predators will be sniffing. What goes around, comes around.

      December 26, 2010 at 9:06 pm | Report abuse |
    • Babak from LA

      Do you know why they other half couldn't see her naked? Because the pages were stuck together!! Hey I made a joke:)

      December 27, 2010 at 7:06 pm | Report abuse |
  10. Joy

    She burst into tears when he gave her the ring. I'd burst into tears too at the thought of marrying that old geezer.

    December 26, 2010 at 7:03 pm | Report abuse |
    • joni

      Ha Ha Joy, good one!!!

      December 26, 2010 at 8:03 pm | Report abuse |
  11. Steve

    No good for her he can't get it up and like the last wife Kimberly she will take him for millions. Hef just does not get it he is the joke.

    December 26, 2010 at 7:04 pm | Report abuse |
    • rod miller

      At 75, I can appreciate looking into the mirror realizing that my assets will be re-cycled to the living who are younger than me. When you have millions why not select people worthy of those assets? I can think of nothing more gratifying than a little tenderness with a good looking honey ... gives a whole new meaning to the term 'living will'.

      December 26, 2010 at 8:37 pm | Report abuse |
    • fhyd

      His estate will go to his three sons, not crystal. She'll get a million and then walk away forever. Like all the girls who get paid out there. No more real than central casting

      December 27, 2010 at 9:41 am | Report abuse |
  12. ialam

    That is just money and that is sick!

    December 26, 2010 at 7:08 pm | Report abuse |
  13. JD

    "This is the happiest Christmas weekend in memory."

    That's nice but I wonder how far back he can remember.

    December 26, 2010 at 7:08 pm | Report abuse |
    • BOB

      Thinkin' the same thing!

      December 26, 2010 at 8:47 pm | Report abuse |
  14. John

    It's hard to tell which is the more pathetic of this couple.

    December 26, 2010 at 7:12 pm | Report abuse |
    • Crocker

      She is by far. Old Hef is just using his money to get some young stuff. The girl must do him with her eyes closed.....

      December 26, 2010 at 7:38 pm | Report abuse |
  15. dave

    i made up a quote : "the desperate house wives, the devil wears Prada- they are one and the same. Lord keep me away from the wicked woman" we all know if he didnt have fame or wealth that girls would not bother thinking about it. their brains are getting more crazy , the phantom, the harry potter, the vampires, they are losing intelligence. not all, but most are screwed up in the brain, then they make bad choices. the Bible clears up the devils thoughts that have seeded and sprout in the brain.

    December 26, 2010 at 7:13 pm | Report abuse |
    • Kate

      This is by far one of the least intelligible comments I've ever seen posted here, and that's really saying something. Congrats.

      December 26, 2010 at 7:52 pm | Report abuse |
    • tah

      and if you were in his situation, you wouldn't jump on that tail too. puh-lease.

      December 26, 2010 at 7:56 pm | Report abuse |
    • Matt

      Next time, remind the hospital staff that you aren't to be allowed on the computers until AFTER the Thorazine kicks in...

      December 26, 2010 at 8:19 pm | Report abuse |
    • Texasboy


      December 26, 2010 at 8:48 pm | Report abuse |
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