Hugh Hefner Got Engaged to Crystal Harris

December 27th, 2010 // 91 Comments

Because what’s one post about a blow to the groin without another? Hugh Hefner has made his most prominent display of senility by proposing to his 24-year-old girlfriend Crystal Harris on Christmas, according to E! News:

Hef tweeted, “When I gave Crystal the ring, she burst into tears. This is the happiest Christmas weekend in memory.”
Not long after, the world’s most famous bachelor cleared up any questions about the ring by tweeting, “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.”
Harris hasn’t exactly tweeted about the engagement, but did post this morning, “Hef and I are TRENDING on @twitter!!!! WOW!!!”

Personally, I prefer to leave a crumpled up pile of bills on the nightstand, but I guess you can “marry” them, too. It’s your money.

Photos: Splash News

superficial

  1. Greenman

    Insert 100 comments/jokes about her only wanting all of his money when he dies because everyone here will think they’re a genius for saying it.

    But honestly, she couldn’t enjoy putting that thing inside her mouth.

  2. Frodo

    FIRST!

    SLUT!

  3. when i saw his name in the news i thot for sure he’d croaked lol. nice one heff do her one for me~

  4. Facebook Me

    Holly just committed suicide..Film at 11..

    • skyehale

      Word. That was my first thought. Some where out there Holly Madison just shit her little bo-peep pants. man, she’s gotta feel bad.

  5. Cock Dr

    Girl’s got a helluva muffin-top going in picture #6.
    Fools.

    • Austen

      Best part is the girl with the stretch marks, muffin top and cheap American Eagle jeans isn’t even her. Take a closer look, Harris is the onlooker dressed in navy in the background.

  6. Rimjob Sally

    But seriously, girls like this must have lower self esteem than Roseanne Barr. Plus you think she REALLY enjoys rimming him?

  7. Hugh Hefner Crystal Harris
    Truk
    Commented on this photo:

    Five years from now this chick will be banging some black dude in front of a video camera.

  8. jojo

    “Mom, my dreams have come true. I’m finally marrying a rich old melted guy!”

  9. I guess sucking on old wrinkled up mummified cock doesn’t bother her as long as she’s being “compensated” for it. Hell IF he does manage to even cum on their wedding night it’ll probably be a tiny flag that says “BANG!!” on it.

    Holly Madison must feel like pure 100% uncut SHIT right about now. ALL those years she played with and sucked on piss and vinegar flavored 500 year old shriviled up balls and he NEVER even asked her.

  10. mcfeely smackup

    She probably said “I’m not fucking you unless you marry me” and he figured he’s only got another 20 minutes or so left to live and negotiating would eat up too much time. So hey, why the fuck not.

    And doing it for the money? Of course…and so what? only poor and ugly people have fair motivations?

  11. Crystal Harris

    Hugh is a sweety and hardly asks for anything, just an occasional blowjob during a diaper change, that’s it.

  12. Hugh Hefner Crystal Harris
    Commented on this photo:

    “Come here post haste, you big sexy creamcicle!”

  13. Hugh Hefner Crystal Harris
    CAPER
    Commented on this photo:

    During sex he declares: “I’m Just In Beaver!”.

  14. Some Girl

    I think I’d burst into tears too if I was going to marry that.

  15. Hugh Hefner Crystal Harris
    Nudge nudge wink wink
    Commented on this photo:

    Do you like anal? Good, because my hemorrhoids can only be treated with suppositories. Let’s get to work, you young filly, you!

  16. Lady Blah Blah

    A lot of marriages are arrangements like the arrangement we assume will be the case between Hef and MS Harris. They just aren’t as transparent and obvious. It’s hard for me to imagine that Hef and Harris aren’t conscious of their relationship being an arrangement where an old fart gets to have sex with a young hottie while the young hottie gets to rise to a financial level she probably otherwise couldn’t, the parties in many similar arrangements (there needn’t be an age differential for there to be similarity) may be totally self-deceived about what is really going on.

  17. j-sin

    Heff ever heard of something called a brunette?

  18. Hugh Hefner Crystal Harris
    Lurker
    Commented on this photo:

    Oh man is Holly going to be pissed!

  19. Hugh Hefner Crystal Harris
    M
    Commented on this photo:

    Sitting there with a bucket of money on her lap, a diamond Playboy bunny necklace around her neck, and she’s marrying that old fuck. I’d say that about sums this bitch up in a nutshell.

  20. Hef's mummified penis

    Barbie Benton was his main squeeze in the late ’60s & early ’70s.
    http://www.celebs-sex-scenes.com/s1/barbie-benton/barbie-benton-011.jpg

  21. GravyLeg

    Publicity for a flagging magazine. Really Hef…
    If you wanna win back the love of the populace, stop dating or marrying them and just give one away to the public. Pretty sure the “Win a Crystal Harris for a year” promo will be a hit.

  22. jt

    she’s the senile one. hef’s got a 24-year-old slice of pie.

  23. Carolyn

    Just the thought of having sex with him makes me ill.

  24. Joyous Kwanza

    Hef is a nasty pervert that has been agrandized by our degenerate society. Actually the media has engendered the fall. All of it has been planned long ago.
    Enjoy your poverty dems and repubs (collection of ignorant morons).

    • Vito

      You are the Chosen One…the Grand Panjandrum…the Grand Poobah! You are the only one out of this mass of ignorant posters who was able to divine, intuit, and translate the political conspiracy encoded in this story about an old man and a super-hot chick.

      Your wisdom and perception are amazing and stultifying. Thank the gods the prophecy came true, and now, at this most exalted season of the year. Thank you again for your incredible insight into humanity, Obi Wan…

      Fucking moron!

    • cc

      “Hef is a nasty pervert that has been agrandized by our degenerate society.”

      I agree with that part of your post anyway. He is gross, and has been for at least 30 years. Then again, the women he’s dated over the past 30 years are equally as disgusting.

  25. Boo Boo Muffin Butt

    She’s a lot better looking than Holly. Bitch looked like Gumby!

  26. atomicmama

    Never seen anybody so proud to catch a prostitute. Not that hard to do Hugh.

  27. Heidi

    Bingo for the Fiancee, is it me or does she look a lot like his first and only wife Kim Conrad (Had to double check), something about her eyes and face and body, even the way she stands smacks of Kimberley Conrad, this new girl is just a littke stringier.

  28. Ned

    I hope she lets him poop on her chest. It took my wife 17 years to let me drop a Cleveland steamer

  29. TracyJ

    What a complete waste of time. Hef I am disappointed in you. Always thought you were the coolest guy around.

  30. You're being roughed with style

    You know whats the difference between me and you? I see this woman as the future economic czar of ( if Bama doesnt drop the ball) our country, you may see her as something else….

  31. xtina

    that girl is NOT 24, i’ll tell you that. she probably has been lying and im sure hef uncovered her real age, but they want to advertise it as low. she looks 34, not 24.

    • babychipmunk

      Yeah she doesn’t look 24
      She actually looks really good in this photo, but in every other photo she’s not great-looking.

  32. If you were 84 and you could, you’d bang every nursing major in Southern California too.

  33. Hugh Hefner Crystal Harris
    still hit it
    Commented on this photo:

    got to get a little dirty when your digging for gold

  34. Hugh Hefner Crystal Harris
    Cock Dr
    Commented on this photo:

    Hef is taking too much Viagra. Why marry this little blonde hustler?

  35. Mel

    It’s like Russian Roulette with these old dudes. Last one married to him when he croaks, wins. But until then… Old man jizz. Ewww.

  36. oldfool

    The joke is on her–Hef has been bleeding money for years. When was the last time any of you spent money on a Playboy?

    • mcfeely smackup

      Hef hasn’t been running Playboy for over 20 years. You’re not big on keeping up with current events, are you?

      That being said, Playboy has indeed been going downhill for a long time…about 20 years, after his daughter took over. Having a woman in charge of a nudie mag has given us such gems as chicks posing NOT nude, and cartoon character centerfolds (also not nude).

  37. anonym

    old enough to be her great grandpa. 60 year age difference!

    picture #3 sums it all up. i.e she’s a gold digger…. and that bucket of money is all she will be left with when he dies.

  38. She was younger when “Schindler’s List” came out, than he was when Schindler’s actual list came out.

  39. Hugh Hefner Crystal Harris
    Commented on this photo:

    “So all I gotta do is touch this old guys wiener for a year or two until he croaks and I get this???

    Done and Done.

  40. Hef is so old, he cums dust. Love the Bang visual.

  41. Vito

    She’s beautiful. I’d fuck her. Hell, I’d probably marry her. But…

    HEF…ENOUGH ALREADY! You’re becoming a sad characture of yourself and the lifestyle you have promoted and espoused over the last 57 years.

    Have all the chicks you want — like you have had over the last half-century. But you don’t need to prove anything to the rest of us. You don’t need to brag. You don’t even need to appear in every single issue of PLAYBOY. We know you are “the Man” and have been for a long time. It’s time to just fade away…

    Buh-bye now!

    • burner

      becoming a sad carictiture?…he has been that way for many, many years, the guy is a perverted douchebag and a sad dirty old Man.

  42. Hugh Hefner Crystal Harris
    Wendel
    Commented on this photo:

    Really?
    This is all the news tonight?
    This is just an embarrassment for all the guys who followed the “Playboy Philosophy” all those years.

    DO the kids from his first marriage have to call her “mom”?
    DO THEIR kids have to call her grandma?

  43. Hugh Hefner Crystal Harris
    Commented on this photo:

    When I think of Hugh Hefner, I think of how he put Marilyn Monroe on the first cover of his then – exploitative, predatory, using females as objects magazine, also called Playboy.
    And then what happened to Marilyn Monroe…
    It was not in Marilyn Monroe’s best interest to be on that cover. Ms. Monroe already had massive national attention already.
    And how Hefner talked that motherless, fatherless, insecure, giant-hearted starlet Monroe to be the sacrificial lamb for his own greed and notoriety is only known to him.
    Ms. Monroe had to live that cover down for the rest of her shortened life.
    At least Hefner is getting married, and not parading around with a harem of ex-stripper Kendras anymore.
    That’s somewhat more gentlemanly.

  44. When I think of Hugh Hefner, I think of how he put Marilyn Monroe on the first cover of his then – exploitative, predatory, using females as objects magazine, also called Playboy.
    And then what happened to Marilyn Monroe…
    It was not in Marilyn Monroe’s best interest to be on that cover. Ms. Monroe already had massive national attention already.
    And how Hefner talked that motherless, fatherless, insecure, giant-hearted starlet Monroe to be the sacrificial lamb for his own greed and notoriety is only known to him.
    Ms. Monroe had to live that cover down for the rest of her shortened life.
    At least Hefner is getting married, and not parading around with a harem of ex-stripper Kendras anymore.
    That’s somewhat more gentlemanly.

  45. Hugh Hefner Crystal Harris
    vomiting from hefner
    Commented on this photo:

    ewwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwww
    isn’t he dead yet???????

  46. Dread not

    That crazy old geezer better bar the doors to the mansion, up the security and check to make sure his two sons are safe. When Holly Madison gets a chance to let all this digest, she’s gonna go full, blown, Glenn Close – Fatal Attraction on Hef’s ass! You know that Holly BELIEVES that should be HER marrying Hef. Hide ALL the Playboy Bunnies, ’cause somethin’ tells me Holly’s gonna want to do some bunny boiling! It’s wabbit season!

  47. Hugh Hefner Crystal Harris
    alsoalurker
    Commented on this photo:

    haha that is EXactly what I thought

  48. wim

    it’s his granddaughter……………………BUT THAT’S O.K.!!

  49. Nik

    he can still bang all the playboy bunnies right?

  50. mr noitall

    If you were to paint Hef purple,he’d resemble one of those lovable California raisins. I forget which one.

Leave A Comment