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Hugh Hefner Puts A Ring On it!

| Filed under: Love LinePlayboy


And we thought wedded bliss wasn't in the cards for America's favorite bachelor!

Hugh Hefner gave his 24-year-old girlfriend, Crystal Harris, a Christmas Eve she'll never forget!

The 84-year-old Playboy founder proposed to Harris after two years of dating. Hef said that she was truly surprised, adding:

"After the movie tonight, Crystal & I exchanged gifts. I gave Crystal a ring. A truly memorable Christmas Eve. When I gave Crystal the ring, she burst into tears. This is the happiest Christmas weekend in memory."

And just to make sure everybody knows that he did in fact get engaged, Hef later said, "Yes, the ring I gave Crystal is an engagement ring. I didn't mean to make a mystery out of it. A very merry Christmas to all."

A very merry Christmas, indeed!

Nothing like a 60-year age difference to keep the romance alive!

[Image via WENN.]

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100 comments to “Hugh Hefner Puts A Ring On it!”

  1. 1

    it is probably for the money that is just like soooo freakin gross and a 60 year difference!!!!!!!!!!

  2. 2

    A 24 year old with an 84 year old — naaaaaaaaaaaaaaaaaaaaaaaaaasty!! Ew! Damn!!

  3. 3


  4. 4

    And somewhere in Vegas Holly is crying in her shower.

  5. 5

    HAHA!! what a joke..of coarse it's for the money and fame..why else would a 24yr old marry an 84 year old? I find it quite pathethic, gross and sad..on both ends

  6. 6

    I have no problem with age gaps of like, 10, 15 years but this is just icky. He's all shrivelled up and she's a bimbo. They are just using eachother. A match made in, um, hell?

  7. 7

    wow…lol.he could be her grandpa.

  8. 8


  9. 9

    Poor Holly Madison she must be so upset. it is disgusting that he is 60 years older than her. doesnt matter who he is thats just gross

  10. 10

    Holly is gonna be PISSED!

  11. 11

    That's gross! 60 year age gap! EWWW!

  12. 12

    Why would ya'll think Holly would be upset? She broke up with him because he wouldn't/couldn't have children.

  13. 13

    Re: Chicken Love – Couldn't have children. They tried in-vitro, everything. And she loved Hef, but children are still important to her. But if they did get married, it could up their ability to adopt…

  14. B2R says – reply to this


    I thought he brokebup with Holly because marriage was't in the cards for him (real meaning: I don't want to marry YOU). Besides, Crystal seems a bit more natural than Holly. Holly dyed her hair to an almost white and wore hoochie clothes.

  15. 15

    What. The. Fuck.
    I mean, he was alive for well over half of a century before she was even born.

  16. 16

    now she can wait until the guy dies and take all his money

  17. 17

    Hef said on an episode of Girls of the Playboy Mansion that he had a vasectomy but had his sperm frozen so he could have children in the future.
    I think this women looks pregnant in this pic

  18. 18

    Oh how wonderful!! It's every 24 year old girls dream to fuck an 84 year old man. However, I'm betting she closes her eyes and thinks of all the fame and fortune that she pays for with her vagina and her mouth and that would probably make it worth her while.

  19. 19

    TRUE LOVE ! ……………… lol

  20. 20

    Re: Chicken Love – Aka, meal tickets. ;)

  21. 21

    just STOOOOPID!

  22. 22

    Oh her parents must be SO SO proud of her.

  23. 23

    My first thought when I saw the picture was that she looks pregnant.

  24. 24

    this girl has so many daddy issues. this is disgusting on a different level. what a gold digger. i seen her in interviews and you can tell she is mentally unstable. and yes somewhere in Vegas holly madison is probably drinking herself into a coma.

  25. 25

    This man must think he looks like a real man to release stuff like this. It is crazy. Who really believes he can still get it up without the help of blue pills? How stupid does he think people are? He just wants to stay relevant forever. Most men at his age are having plaques put on buildings, but this guy thinks this is the way to do it.

  26. 26


  27. 27

    My 85 year old father thinks Hef is a nutjob.

  28. Beccx says – reply to this


    Hef only marries the ones that swallow.

  29. 29

    She gives him one hot fuck, his heart expires, and at that time she has him sign a will giving her everything. Smart cookie ! I mean, the man is SO old, he doesn't leave finger prints ! His prom theme was FIRE. She calls him 'Hun', because he was one ! He can name all the American presidents by memory because he was alive for most of them ! Just say'n ……

  30. 30

    Re: YoBellaBella – The girl has DADDY issues … ? ! ! Try GRANDFATHER issues !

  31. 31

    I wonder what her great grandpa thinks. He should be around Hef's age. UGH>>>>
    There are some things one should NOT do for money!

  32. 32

    Gawd, is he ugly ! I know he is old, but, wow…UGLEEEEEEEEEEEE ! She must reallyt need the money to fuck that ole thang ! Can you just picture her going down on him ? Halfway through, with his poor memory, he probably shouts out: I thought you were going to get me my Metamucil !

  33. 33

    Old people smell - she must really be splashing on the Chanel #5 when with him!

  34. 34

    I am sure they talk about a lot of things…Music, Art, Politics, and, for him, HISTORY. Lord knows, he knows A LOT about that subject ! He has been around for most of it ! !

  35. 35

    Holly: go get 'ur gun!

  36. 36

    good for them… Holly always had a crazy look in her eyes… this one seems sweet or looks it!

  37. 37

    eww…eww…and, eww…

  38. 38


  39. 39

    So, they've been "dating" for two years, whatever that means. If she's not pregnant, she must be terribly constipated, do take some metamucil blondie.
    Hate to admit it but HH doesn't look his age, he looks about 69. Go for it you Prince Charming ? HO ! HO ! HO !

  40. 40

    hahahah he should be in a convelescent home flirting with old ladies. Well. money talks and money does miracles.

  41. 41

    is it me, or does his child bride look slightly preggo in this pic??? hmmm. yeah, Holly has to be super jealous…she tried to land him & make babies for years! i give the marriage 5 years….only because he will croak before they divorce. what a gold diggin' ho

  42. 42

    the happiest memory in memory? God at his age that could mean since lunch! Oh no, Iam sure, his sex appeal reaches women of all ages (yawn) I think its the digits of his bank account that reach women of all ages…but what do I know… I am just…you know….sane

  43. 43

    These whores must smile for the cameras but i bet they cry themselves to sleep every night

  44. 44

    I wonder who got her pregnant.

  45. 45

    Re: gimpus maximus! – tHEY JUST CLOSE THEIR EYES AND THINK OF…the money ! ! !

  46. 46

    pedifile, gross, grandpa…84 years old..24 year old wife????

  47. 47


  48. 48

    Re: erikasjammin – or great grandpa

  49. 49

    This girl is obviously waiting patiently until Hugh dies so she can get her hands on his money. Why go for crinkled old cock when you can easily get WEALTHY hot young meat…?
    Hugh Hefner isn't as rich as he used to be, either. He's had to cut staff at the Playboy Mansion and his business hasn't made as much as it used to.

  50. JCPR says – reply to this


    she must be like yay finally im gonna be rich! can't wait for this old fuck to die and ill keep all of his money! this house will be MINE! buahahahahaha lol

  51. 51

    What can I say?

    She is blonde!

  52. 52

    All I gotta say about this is poor Holly. She tried for years to get him to settle down with her and he didn't want to. I guess Heff just wasn't that into her.

  53. 53

    They look gross as a couple & not couple like at all! It's not for the fame he says. MY ASS!

  54. 54

    Another token with a WEAVE. Tired. Next!

  55. 55

    that is so disgusting. his first marriage ended in 1959… like 30 years BEFORE she was born!

  56. 56

    Re: B2R – Natural? Crystal? bwahahahaha Girl is not natural. She has had multiple plastic surgeries and dyes her hair too, just albeit a more natural looking blonde than Holly dyes her hair. Feel free to look up pics of Crystal. She dresses trashy just like Holly. Holly dresses more Vegas trashy and Crystal more trailer park trashy.

    Looking "natural" would not be a reason for Hef to like Crystal over Holly. Hef tends to like the un-natural look (see pics of every girlfriend since his marriage broke up). Also, Hef said he and Holly broke up because Hef couldn't have kids and Holly really wants them.

  57. 57

    I was just watching a re-run of girls next door and it was one with Holly and Crystal…Holly spent 8? years with him…which sounds kind of unpleasant to begin with and then she leaves and two years later he's engaged to a 24 year old? that sucks for Holly even if she wanted to leave or w/e. An ex moving on always sucks…

  58. 58

    What the fuck????? so he had Holly devoted to him for like 7 years and never married her because "that wasn't in the cards for him" and now he marries the first playmate that he picked after Holly???? i HOPE this girl takes all of his money! he deserves it for being THAT stupid! ;)

  59. 59

    she looks knocked up

  60. 60

    She doesn't seem like a publicity hound like Holly, but the age diffrence. I am sure Hugh is a nice guy and has given her many material things, but she should be around someone her own age.

  61. 61

    wonder how Holly feels caus she rally wanted 2 marry him but he didn't see that kind of commitment.

  62. 62

    I bet Holly's PISSED!!! She tried her hardest to get him to commit to her!!! I'm sorry, but I just don't see what kind of connection you could have with someone that much older than you…I mean, I'm sure it's for the money, but let's face it… Hugh Hefner isn't stupid…he's a smart businessman…There will be a prenup!!!

  63. 63

    she looks pregnant!

  64. 64

    Re: erikasjammin

    He could be her great grandpa……

  65. 65

    pretty yucky.

  66. 66

    Oh come on, this man is such a pimp, he knows he's getting played by gold diggers, you think he cares? He's incredibly rich and hot skanky girls throw themselves at him. He's 84 and he gets more action daily than most of you. One day Hugh Hefner is going to decide his life is complete, lay down in his best silk robe on a bed of the finest cloth, and die the happiest man who ever lived.

  67. 67

    there is no fool, like an old fool!

  68. 68

    I hate to spoil all your fantasies people - but this is nothing to do with love!

  69. 69

    Is she knocked up?

  70. 70

    Re: cheerprincess99 – Yeah. If they make it down the aisle, she gets everything when he dies in what 5 yrs?

  71. 71

    Who cares how old he is, Hugh Hefner is pretty unique for his age. He is pretty hip as well, smokes chronic and is very liberal. Haters hate.

  72. 72

    ha… i bet holly is PISSED!

  73. 73

    jeeezus……that dam hole will do anything for $$

  74. 74

    *sigh* There's no true love except for Hollywood love.
    Now if you'll excuse me I need to shut down.

  75. 75

    he's gonna die soon, way to gold dig bitch!!

  76. 76

    Is she pregnant?

  77. 77

    Re: Theresa Montez – looks it… that would be very amusing.

  78. 78

    Holly was just waaaaay to old for Hef.

  79. 79

    True love? I think not. This is just plain disgusting, and whats worse is she looks pregnant in that photo, lets hope they dont have any kids, no child deserves to be stuck with these two idiots as parents.

  80. 80

    Re: erikasjammin – Correction: He could be her Great Grandpa!

  81. 81

    in the words of kanye - i ain't sayin she's a golddigger…………..

  82. 82

    I bet Holly is Pissed!

    And isn't he still married legally married to Kimberley Conrad? She lives in the house next door with their two sons. Ridiculous.

  83. 83

    Pooooor posture. Chick's got pelvic tilt major! That in and of itself is naaaasty!

    Hey, I say more power to her - M.O.N.E.Y., baby! If all she has to do is sleep with that smelly ol fossil to gets millions, eh, hit it, girl! HAAAAAAAAA

  84. 84

    if she met him in a restaurant and his name wasn't Hugh Hefner- do you really think she would have even taken the time to talk to him

    and Hef's daughter is and will be running his empire after his death and inheriting most everything–that being said- with his $ I'm sure he can provide well for anyone else he choses-friends, wife, charities etc.

  85. 85

    Of course the 24-yr old cried when she agreed to marry the 84-yr old.

  86. 86

    i'm really sad for holly……

  87. 87

    Re: Grace Equality Pheiffer – LOL thats what I was thinking.. Holly was with him for sooooo long (in Playboy girlfriend terms that is) and wanted so desperatly to get married… and this new one waltz's right in and seals the deal. epic.

  88. GiaB says – reply to this


    I LOVE that he said marriage wasn't in the cards for him again and Holly bolted! Looks like this one might not have pressured him. I say good for Crystal!

  89. 89

    Holly begged him to marry her, go figure!

  90. 90

    Holly is so jealous right now.

  91. 91


  92. 92

    I hope they don't have kids….his sperm use a Jazzie to travel.

  93. 93

    Ewwwwwwwwwwwwwwwwww. I just threw up my dinner. He's too old and his pee pee is infested with STD's. Women can be nasty whores with their holes. Damn. Gross.

  94. 94

    who's your pop pop?

  95. @v@ says – reply to this


    There's no fool like an old fool.

  96. 96

    Hefner is now part of history - The age thing is just prejudice planted at different ages in all cultures - If this woman can give him a child, then he did what he has always wanted to do - If she marries him for whatever reason in the universe, she loses nothing - Good luck to the old hip revolutionary and his bride…I say

  97. 97

    tears of JOY, that bitch set 4 life

  98. 98

    she was probably crying, because she knows shes set for life with all that money… How disscusting, and he's all old..

  99. 99

    Prenup! Prenup!
    no worries about breeding cause, come on, how old is he??!!

  100. 100