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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 (1,631 Responses)
  1. AussieLion

    Armchair critics! Get a life! Raggin on the old guy then raggin on the young chick. You'd be calling it something entirely different if he was broke and she was ugly!

    December 26, 2010 at 11:38 am | Report abuse | Reply
  2. werner

    this poor old fool, has never experienced love in his entire life. When i die i will be ready to go, having fullfilled my live with love and happyness. I belive when he goes, he will be freaking out....totally scared of death. He will be paying doctors lots of cash to try to keep himself alive....

    December 26, 2010 at 11:39 am | Report abuse | Reply
  3. saywaaat

    if hef was a moslem ,all of you would sing a different tune.

    December 26, 2010 at 11:41 am | Report abuse | Reply
  4. Same old same old

    Funny how we don't see the "ring" on her finger

    December 26, 2010 at 11:41 am | Report abuse | Reply
    • El Kababa

      I think that is a file photo from some time in the past.

      December 26, 2010 at 2:34 pm | Report abuse |
  5. redwing1

    RIDICULOUS!!!!!

    December 26, 2010 at 11:42 am | Report abuse | Reply
  6. Phil

    He's not a sugar daddy.

    He's a sugar great grand daddy.

    December 26, 2010 at 11:42 am | Report abuse | Reply
    • Aarrgghh

      Darn near a "Sugar Mummy" lmao

      December 26, 2010 at 12:16 pm | Report abuse |
    • Jerkin The Gerkin

      He's just a creepy old dude with too much money and no class. Nothing more.

      December 26, 2010 at 12:40 pm | Report abuse |
    • Matt

      Hugh has had various health problems that are public knowledge. I'm not privy as to the exact diagnoses of them, but in articles that I have read in magazines and online, I recall reading that he has suffered at least 1 incidence of stroke and 1 prior myocardial infarction (heart attack). Do you know that one of the easiest ways for men to have erectile dysfunction is a prior cerebrovascular or cardiovascular event such as a stroke/MI? So, he can pop all the Viagra that he wants, but he also has to be concerned about myocardial ischemia when attempting to have s-x. Of course, s-x isn't overly laborious (equivalent to walking about 4mph). I run at 8-10mph for hours!

      December 26, 2010 at 12:42 pm | Report abuse |
    • Juan Garza

      @Aarrgghh HAHA Good one!!!!

      December 26, 2010 at 12:47 pm | Report abuse |
    • Ellen Hunt

      You know, for all of you that believe in evolution, "The Hef" is batting 1000. You see, we humans, we have astonishingly long life spans. Gorillas last 35-50 years and chimpanzees 30-40. In the wild, we humans live 80-90 years. (Different from average, which is pulled way down by child and infant mortality.) So evolution requires that something moved our life span. The only reasonable idea is that old men made more prolific fathers. So all of you monogamous guys who breed when you are young – you are pulling down the human life span by force of evolution.

      December 26, 2010 at 1:12 pm | Report abuse |
    • Pete

      Shows how women are so Ingeneously so desporate. Fake nails, boobs, make up, hair, & above all Self Esttem. So Many of wich cannot stand on thier own two feet & have a real LIFE & / Or PERSONALITY. So Phonny & Plastic. Let Me Guess ?? Suicide By 25 DAH DAH DAH !!!

      December 26, 2010 at 1:23 pm | Report abuse |
    • NimrodNorm

      She and Hef will be having two lovely, gifted children, and they'll all live happily forever in Playboy Land, beyond the sea. Hef told me that's their plan, and he's always right, because I KNOW!

      December 26, 2010 at 1:28 pm | Report abuse |
  7. splasher6

    proving yet again women are all about the money... you never hear a man say yea I'd like some of that Roseann Bair...

    December 26, 2010 at 11:42 am | Report abuse | Reply
    • AlB

      She was thinking smart....hes got no more then 10-15 years left on him....i wonder who will get all that money when he pass's,lol

      December 26, 2010 at 12:00 pm | Report abuse |
    • Oh

      "you never hear a man say yea I'd like some of that Roseann Bair..."

      Thanks to the internet, we sure do, and the proof is in pictures!

      December 26, 2010 at 12:19 pm | Report abuse |
    • dot

      it really proves once again men want a young stupid thing......

      December 26, 2010 at 12:20 pm | Report abuse |
    • Amy

      She's another Anna Nicole Smith...

      December 26, 2010 at 12:36 pm | Report abuse |
    • TJ

      Right because young men never marry rich older women for their money. Please. How about "it's about the money. PERIOD."

      December 26, 2010 at 12:39 pm | Report abuse |
    • vejendisko

      well were not poor, we just need help. they live in stink flourplans like animals. i'll never be poor, you just dont know how much money it is. you kill their son, and take their money only

      December 26, 2010 at 1:02 pm | Report abuse |
    • Ellen Hunt

      She is a material girl ...
      And this is a material world ....

      Married rich, married poor. Believe me girls, rich is better.

      December 26, 2010 at 1:13 pm | Report abuse |
    • WR2

      @vejendisko
      Wrong thread dude. The thread for the emotionally disturbed is over on Fox.
      WR2

      December 26, 2010 at 1:21 pm | Report abuse |
  8. Me

    You know who she sort of resembles...? Put her in a dark wig and stand her next to Michael Douglas.

    December 26, 2010 at 11:42 am | Report abuse | Reply
    • runner305

      good observation! ur SO right!!

      December 26, 2010 at 11:53 am | Report abuse |
    • Mike

      Your absolutely right. Same wide eyes, full figure. Great perception.

      December 26, 2010 at 12:13 pm | Report abuse |
    • chris

      You are exactly right. Extremely close.

      It was my thought when I first saw the picture, just didn't put it into words like you. Good job.

      December 26, 2010 at 12:30 pm | Report abuse |
  9. Brad

    Hefner is the true James Bond

    December 26, 2010 at 11:43 am | Report abuse | Reply
  10. Airwaves44

    Way to go Hef.....you'll always be my hero!! I'm sure the lawyers drafted up a nice pre-nup for the wifey LOL.

    December 26, 2010 at 11:45 am | Report abuse | Reply
    • sam

      nice hero, loser

      December 26, 2010 at 11:54 am | Report abuse |
    • MLW

      PATHETIC HERO

      December 26, 2010 at 12:04 pm | Report abuse |
    • Aarrgghh

      I suppose it is a better hero than some 20 year old who shot a few people in the face... Ie: soldier

      December 26, 2010 at 12:23 pm | Report abuse |
    • hefnyes

      little bit of resentment over there buddy?

      December 26, 2010 at 12:31 pm | Report abuse |
    • Just Shellz

      He's disgusting! No way around it....

      December 26, 2010 at 12:51 pm | Report abuse |
    • shawn

      Lol! a pre-nup isn't nothing that a judge cant throw out or change. He's an old fool to think she wants him and not his money. men like this help golddiggers thrive cause its always a low self esteem, small in certain areas man willing to compensate for their shortcomings

      December 26, 2010 at 12:55 pm | Report abuse |
    • Rick

      Well, that's one good way to go out with a bang...

      December 26, 2010 at 1:00 pm | Report abuse |
    • Buck

      IDIOT

      December 26, 2010 at 1:13 pm | Report abuse |
  11. Robin Thomas

    No way she loves that old man.

    December 26, 2010 at 11:45 am | Report abuse | Reply
    • Becca

      NOPE! But she looks like she loves money.

      December 26, 2010 at 11:57 am | Report abuse |
    • rmsbl4

      I bet she will hide those little blue pills as soon as the get married.

      December 26, 2010 at 12:36 pm | Report abuse |
  12. DS

    Vanity and Greed

    December 26, 2010 at 11:49 am | Report abuse | Reply
  13. cm

    maybe he can have another kid...then he will be 103 when they graduate highschool..

    December 26, 2010 at 11:51 am | Report abuse | Reply
  14. joe harrington

    May-December? more like late January-mid-December. beam me up...

    December 26, 2010 at 11:52 am | Report abuse | Reply
  15. werner

    Just a glorivide PIMP.........But not his fault, he was raised without love.......actually a very poor lonely rich man

    December 26, 2010 at 11:53 am | Report abuse | Reply
    • tk

      Oh how I'd love to be a poor, lonely rich man then.

      December 26, 2010 at 12:10 pm | Report abuse |
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