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. sexybitch

    #50 That’s because all of the camera crew’s footage of Kimberly was of her sticking pins into a doll and screaming, “Die, you sick wrinkled fucker, DIE!” Kind of ruined the mood.

  2. HollyJ

    Is that Thurston Howell III ?

  3. wtf

    Don’t forget..tonight is enema and suppository night Heffie!

  4. 23apples

    I personally hope this isn’t true, becuase I love the show and Holly is by far my least favorite girl of the 3. She is weird looking, doesn’t have a fun personality, and seems the fakest out of them – she might be the one who looks like she cares about Hef the most, but uh, when your a fake person, that wouldn’t be hard to pull off.

    I really love that the show always shows Bridget & Kendra giving way less affection for Hef than Holly.. probably because they get the urge to vomit when thinking about him in a sexual way – like every other normal person does.

    #30 – HAH!

  5. Lowlands

    ‘Even when you’re surrounded by the most beautiful women,you’ll be in need with one you can consider your wife’.Genius!Thanks again mr.Hefner for your message filled with almost a century of wisdom.I’m suddenly urgently looking for a girl which can cook,doing housekeeping and laundry and private administration.Where are thou?!

  6. Holly Madison: “I’m excited to marry Hugh! Sure, he’s got a lot of money. But I’m 27, and with Hugh I’ll be able to experience what it’s like to be a mother because I will be changing his diapers, helping him walk, and ultimately, I’ll be putting him to sleep.”

  7. Defcon

    lmao to true love, lots of money, and fake tits.

  8. The bitch has father issues clearly…I guess her real dad didnt give her enough attention when she was a kid or he gave her too much attention if you know what i mean

  9. Cardinal Ximenez

    Hmm, according to Jill Spaulding’s book, girlfriend #1 is the GF that is obligated to have anal sex with Hef. Yep thats what the book says.

    That just makes it all the more creepy, she’s getting ass banged for the money.

    “He has anal sex with his real girlfriend and all the other girls cheer. As soon as he’s finished, everyone just disappears and his main girlfriend and him start to make out. Rumor has it that a doctor comes in and checks on him after the girls leave the room, but I didn’t see that.”

  10. Juliabella

    At this point, she probably feels less when they have anal sex then she does when it’s time to say goodbye to yesterday’s bean burrito.

  11. NipsyHustle

    holly deserves to get a ring because she’s been riding this skeleton for 5 years. that is dedication. i’m sure he’s not going to be leaving her much though. hef said it himself. the whores keep him young. settleling with this hooker is going to put him in the grave.

    of course kendra hates hef. she only likes thug ass black men. she only loves black cock…period!!! i’m surprised she loves cock at all considering how butch she is.

    and brigette better get going on starting her “broadcasting career” because those crows feet around her eyes are so deep, i’m tempted to plant some maize in them. that bitch is old!!!!! she’s 31 or 32 which is way beyond hef’s 25 y.o. expiration date.

  12. Truthseeker013

    Dear Mister Webster,

    Find attached photograph regarding subject “redefining obscenity”.

  13. Courtney

    Just because she’s the hottest does not excuse the fact that she’s like, the dullest person ever. How do some of you honestly think she’s the most interesting? But it figures she wouldn’t like Kendra. Boring girls tend not to like the fun ones because they get all the attention.

  14. Courtney

    #59 – indeed. Classy girls take it up the butt for coke.

  15. Mick

    I watch the show because.. it’s addictive, I guess. I thought Holly was the prettest of his girls. I really don’t like Kendra, she’s ugly and annoying. That quote above in the story is confusing a bit though, is it hef or holly that hate kendra? I’m guessing kendra and holly hate each other and play nice for the show.

  16. fame is funny

    Hef’s nickname is ‘Captian Stubing’ and he’s ready to sail the seas…of tits.

  17. pixel killya

    @18 – danielle <-you stupid cunt.

    Since when do “Priceless” commentaries include “checks” instead of prices?

    Mine was a wedding checklist, you cave-dwelling loser.

  18. fame is funny

    don’t worry, danielle has something stupid to say, you’ll get used to it.

  19. lol at that stupid sailor hat and heck, their entire lives for that matter.

  20. my opinion

    Thanks for the entertainment! These postings are some of the funniest I’ve read on any blog.

  21. williedisnotabigot

    Motherfucker look like Popeye.

  22. licklick

    I don’t like Barbie Doll hair.

  23. sid

    Beyond parody, like the pic of The Hoff in drag, next to his own cardboard cutout.

    Heff has got a billion dollars, and Viagra.

    Take a look at the pussy a freak like Quentin Tarantino gets.

    Bitches will fuck a bucket of mud if it has money.

    Haters, step aside. He’s rich and can afford a better hardon than what you have, and he plows it into something hotter than your best girlfriend.

  24. EliasAlucard

    Of all his extremely beautiful “girlfriends”, he chose to ‘maybe’ marry the ugliest one.


  25. Sinthe

    He can’t marry Holly. He’s still married to his ex-wife from whenever. They never divorce, and I doubt Hef is a Mormon.

  26. wink

    Money ALWAYS wins out

  27. RodneyOverLord

    Bridget will probably be kicked out the house after the show is done. She’s there as a freeloader & trying to be semi-famous. Kendra is just dumb & young, she is a feisty one but she wants to be black. Notice how whenever the black athletes & rappers come by, she always hangs with them? Also, she used to post on Terrell Owens forums all the time! I wouldn’t be surprised if she met some rapper or athlete & left Hef. Holly on the other hand is devious but she’s the most committed & actually loves Hef.

  28. Courtney

    #77 – you know, just because people enjoy hanging out with people who happen to be black doesn’t actually mean they want to be black themselves. They might just not be the huge racist idiot that you are. Try leaving the suburbs every once and a while, won’t you?

  29. RodneyOverLord

    #78 have you watched the show? She wears grills, all she does is listen to rap, she sticks her ass out & does the booty shake dance like you see in rap videos. Let me see, I wonder maybe you fit into that category & got insulted/defensive? I’m not a racist as I have some black friends. I leave the suburbs a lot as I live in a urban downtown setting.

  30. Tammara

    Is that Bob Barker?

  31. Courtney

    Hmm, dunno if downtown Minneapolis necessarily fits the bill of urban living, but that’s cool. And you know, the standard defense for racists is “I’m not racist! I have black friends!” Way to be apropos on that one. But the very fact that you consider certain things to be either black or white behavior speaks volumes. You, my dear, are prejudiced. Have a lovely day.

  32. burningsensation

    Oh, how sad. It’s the Skipper and I think he has cancer.

  33. RodneyOverLord

    Downtown Minneapolis? No, I live in Downtown Miami but I am located in Atlanta right now. It might be the standard defense saying I have black friends but would a real racist actually have any black friends? And who isn’t prejudiced? Everyone in some way shape or form is somewhat prejudiced, some more than others. And yes I can categorize if certain thins are either black or white behavior. It’s called observation & from observation I noticed that certain groups tend to behave in certain ways (both in the real world & in the media). For example, there are guys you know of that watch anime 24/7 & love all things japanese, considering them wanting to be japanese would be considered racist? I don’t see the logic.

  34. Mick

    I think you are all racist 77-83.


  35. hotintempe

    Maybe she likes being around black rappers and athletes because she knows they have at least a 12 incher between their legs.

    Is Holly hispanic with blonde hair?

  36. hotintempe

    Maybe she likes being around black athletes and rappers because she knows at the very least they have a 12 incher between their legs….ha ha

    Is Holly hispanic with blonde hair?

  37. Who Gives a Fuck!!

    Fucking ridiculous Old Hag…And the Blond gold digger, sans personality Hooker Barbie wannabe….congratulations….you sure nabbed yourself a 24/7 fucker, congrats on the mind blowing sex!!!

  38. Slinxter

    Photographers will be snapping photos of her in a years time brandishing bent and broken umbrellas after shes has his offspring, note the “OFF” in offspring.

  39. swerx

    I can’t believe people are talking about this like it’s real. It’s show business folks. E pays millons (yes millions) to Playboy for access to the mansion and Hugh’s life. The relationship between Hugh and the girls is an invention, nothing more. I’m really stunned people believe a guy who is eighty something is hacing sex with a beautiful twenty-somethings.

  40. mikmel

    i think that holly is the best looking out of the three and from watching every episode of the girls of the playboy mansion as it is called here in australia, i think she does love him. why else would she share a room with him whilst the other two don’t and why else would she talk the way she does about him. and of course they have sex he would be stupid not to

  41. yeah, sure….why not just die already

  42. HollyWaffle

    Holly is hot and smart, obviously she’s in it for the money and good on her, God knows she deserves every penny for having to kiss this man, even if it’s just for the camera and she also deserves it for putting up with that retard Kendra who is wasting oxygen by being alive.

    Oh wait I take that back, Holly is dedicated and loving, she cares for Hef not for his money or fame. She would love this 82yr old man even if he had no money and lived in the gutter. Kendra still sucks butt though, not taking that back.

  43. Missystar

    I love the show, it’s good mindless entertainment. Here’s my two cents: Kendra Wilkinson is the biggest cretin ever to walk the face of the earth. She seems to firmly believe that she is the sexiest thing ever, despite her hyena laugh, big nose, and thin lips.( There’s a lot more to seduction than how you look, for one thing.) It’s really a pity that Bridget is going nowhere, she seems like a genuinely good-hearted person. As for Holly– oh my sweet lord, what a robotic, blank-eyed weird bitch! It’s odd because she does appear to have a sense of humor–she cracks jokes and everything, BUT HER EXPRESSION NEVER CHANGES. But of course, none of this really matters because I’m sure if HH was some typical senior citizen, living in a trailer and eating government cheese, they’d still want to hang with him, right? Right???

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