Hugh Hefner maybe marrying Holly

February 26th, 2007 // 93 Comments

claims the buzz during the Oscar parties was that Hugh Hefner is getting married before the end of the year to Holly Madison, one of his three girlfriends.

“This is very secret, but the word is ‘yes,’ ” one insider told Page Six. “Hef has decided he will marry Holly, and he wants it for his show, ‘The Girls Next Door.’ Hef thinks business all the time, and looks for a new hook, although he also does really love Holly… Hef sees that she is the most dedicated. Kendra is never there, and they both hate each other, and Bridget is hanging on by being very friendly to Holly.”

That Holly sure is a lucky gal. She gets to marry a guy who’s just, what, barely in his 120′s? And has two other girlfriends? And looks like E.T.? It’s like every little girl’s dream come true. They should write fairy tales about her life.


  1. Danner

    Lucky old bastard!

  2. sarah

    and will probably reel over soon, leaving her the money

  3. Anexio

    Jaysus, he could so much better than her.

    I bet Hef’s parents will be disappointed.

  4. elizabeththewellread

    When I first started hearing about their “true love”, I thought, Well, maybe. . .”

    Apparently not.

  5. EveryoneBugsMe


  6. sikofdis

    Say what you will about Hugh being old, but at least he’s still a great dresser…

  7. llllllllll

    He chose the small headed ugly one. Way to go Heff

  8. I always thought Gilligan was gay…?

    oh, and…I GOT EI8TH !

  9. Stink

    #6 He’s dressed like Mr. Howell! Now he’s gotta call her ‘Lovey’ and secretly poke Ginger and Mary Ann on the side.

  10. So Kendra and Hef hate each other? Don’t you usually not have girlfriends who you hate?

  11. jrzmommy

    She’s extremely odd looking. I’m sure she’s got a few extra chromosomes.

  12. Binky

    Hey don’t his outfit. This was Halloween. He was ‘The Captain’ and she’s a personal flotation device.

  13. Kayleigh

    oh no! the crazy one is going to get her way?

  14. serial snarkalec

    It’s the Anna Nicole Show sequel. Naw, we haven’t heard enough about that.

  15. llllllllll

    Shouldn’t Heffs pants be at least a couple of ribs lower? I don’t know, maybe it’s just me.

  16. omelette ze roar

    Ewewewewewewewewewewewewwwww!! D’:

  17. pixel killya

    Platinum blonde dye job – check

    Big fake tits – check

    Fluorescent white teeth – check

    IQ of shag carpetting – check

    Willing to do cadavers – check

  18. danielle


    Retarded overplayed Priceless commentary – check!

  19. danielle

    And to be on topic,

    if y’all take a look at her face, she’s got a large forehead, and a very masculine nose.

    Just sayin’!

  20. neonink

    #9 very good observation.

    (ps. she acts as old as him. but i like her the best too…)

  21. I ain’t saying she’s a golddigger,
    But she ain’t messing with any other 80-some-year-old men with a multi-million dollar magazine empire.

  22. Stink

    #19 I’d force her to wear make-up to bed. I don’t wanna see what’s underneath…

  23. fritobandito

    Wow, it’s like Weekend at Bernies! I am pretty sure Hef is already dead. Thats why the capn’s hat, it hides the concave part of his skull. At least until after the wedding! And here I was worried there wouldn’t be anyone to take ANS’s place! Howard K, better get his ass back to the states and make friends with Holly!

  24. veggi

    Where’s his pipe? And that my friend is not Oliveoil. She’s gonna be pissed.

  25. Wow Just Wow

    They look alike.

  26. belinda

    What’s the big deal? To get at his money, lots of girls would be willing to choke down the dust that comes out of his shriveled penis after 60 minutes of jaw-cramp sucking.

  27. xXrebeccaXx

    I think Holly is gorgeous. If she wants to marry an old guy so what!?!?! On the show it seems like they really love eachother. Holly seems to look past the old body and love the romantic man. So what’s the big deal??

  28. meee

    holly is gorgeous and from the show she seems sweet and she always says something/cute/stupid to make me laugh. i hope they do get married because you can tell how much she wants it.

    however i think this source is probably bullshit. i bet there aren’t major problems with kendra or bridget. and if the source IS real and correct, then that person is a fucking asshole for letting the cat out of the bag so early.

  29. RichPort

    ANS Part II.

  30. MrSemprini

    I was at the manse recently and let me tell you, these two are really in love. Holly never goes anywhere without Hef, or at least, some part of Hef. He’s got enough detachable parts that Holly and Bridget and almost share him. Kendra just gets a foot every other Wednesday. HA ha. I know, its not that funny but with Hef, everything’s a laugh. Like the time Holly took her makeup off for a Brazilian wax. Hef walks in without knocking and bang! What a laugh as everyone tried to figure out how to work the defrib machine. Kendra was saying that they could take him to the garage and use jumper cables. After the fun died down, Bridget reminded Holly that she still had to do the Brazilian and Holly said, “No, its just one wax job. I can’t imagine how to count in Portugese. I’ve never learned how many are in a Brazilian”. Everyone laughed while she looked cute and kept saying, “What?”. Then Kendra offered to tighten her corset. By then Hef was awake enough to mumble his favorite three little words, “Call my lawyer”. What a great bunch!

  31. renestel

    Do you think she just sees his countless lines and wrinkles and lets them resemble stacks of cash she’ll get while she’s having sex with him? How does this woman ever flippin’ get off?
    I think she’s Ursula from The little mermaid. Right when he marries her, she’ll split her skin and ooze out to show her big fat rolls and evil witch face, and of course the soulless cackle.

  32. jFp

    Why is he picking the fugly one? Actually I think they don’t make skanky whores like they use to. These 3 look like trailer-trash that broke into Tammyfey Bakers clown-kit. Really, that blonde-bomb thing went out of fashion with the Gabor sisters 40 years ago.

  33. LL

    I’m glad I’m not the only one who wonders what’s up with that ridiculous hat. I guess when you’re old enough you can wear whatever you want, but… damn, man.

    About the marriage rumors, who gives a rat’s ass? Yeah, same sex marriage would be the end of civilization as we know it, but Barbie can marry Mr. Howell and that’s A-OK. Just sayin’. Yuck. There’s not enough money in the world to let any part of Hefner’s body near me. He’s always been sorta icky, so it’s not just the age, but that is a big part of it.

  34. lambman

    Good for him, Holly is by far the best of the three girlfriends. She’s the cutest for sure, and appears to be the only one who remembers Heff exists when he’s not in the room.

  35. whitegold

    Holly is friggin smokin hot, and she actually seems to have a good personality!

    Do they have sex though? Can Hef still have sex? Is it wrong that I’m wondering what the sex life of Hugh Hefner and his 3 girlfriends is like? Cuz it does make me feel a little dirty, and not dirty in the freaky sexy way, but rather in the unpleasent pervy way. But seriously, he has some fine young ass at his disposal, and I can’t help but wonder how he works it, if at all.

  36. queenbuzz

    Look everyone it’s Ho Hefner!

  37. Jenster

    she IS the prettiest of the three.
    The girl needs some god damed self esteem though.

  38. sexybitch

    #21 ed87, that was perfect! LOL

  39. xXrebeccaXx

    jFp…..I agree that the blonde bombshell thing isn’t in right now…but Hef likes it. So obviously …the girlfriends need to keep that up.

  40. WTFiswrongwithUppl

    Oh boy, can’t wait to watch Holly duke it out with Hef’s kids after he bites the big one. Maybe she will spawn and ugly little old man-baby with Hef, thus prolonging the drama and court costs.

    How come all of this sounds so familiar? Deja frickin vu.

  41. WTFiswrongwithUppl

    Ah shit, I’m too lazy to correct my typo…

  42. Gina

    She’s smiling like the cat that just ate the canary’s enlarged prostate.

  43. Carsten5577

    Do you think the whore really loves him or doing it for the money? I dunno…

  44. His other girlfriend Kendra is so obviously a lesbian that this is the PERFECT situation for her…

    Hef is too damn old to fuck her and she gets to play “Licky Licky” with the other two publicity stunts…oh pardon me “Girlfriends” “Wink Wink”

  45. swerx

    Hate to burst the bubble, but I used to work at Playboy. It’s all a publicity stunt. When the cameras are off it’s all business there, and the girls (when I was there) all have real boyfriends. Hugh is smart, and he knows people believe whatever they see on television. Although the having a child thing may be real. Although they don’t have sex with him, I’m sure one of the girls would be willing to be artificially inseminated with some of Hugh’s frozen sperm in exchange for a lifetime of financial security. Hell, I’D do it if I could.

  46. Nimuë LaMer

    She may be the funny looking one out of the bunch, but she’s the one who knows CPR and is hiding those electro-paddle things under those enormous breast shaped covers.


    beeeeeeeeee… beep beep beep beep beep beep beep…

  47. #38 – Thank you, I’m here every other day. :-p

    I’m sorry but I don’t see what people see in her. She has a man-chin and man-nose. Sure she has gazongas but those are fake, I’m sure.

    In other news, #40 hit it right on the head. Deja vu.

  48. RichPort

    That big nose is unfortunate because you know Hef has the intense old-man smell.

  49. … you know, that strong musky smell at the base of the shaft, above the testes, particularly noticable after your guy works out?

    I mean, um, … that’s what I heard. Really.

  50. miscellany

    Isn’t Hugh Hefner still legally married to his wife Kimberley Conrad? They’ve been separated for a very long time but last I heard she was living next door to the mansion and they hadn’t filed for divorce yet. Funny how they never mention that on the show when Holly is coyly hinting at her desire to marry him.

Leave A Comment