Holly Madison and Hugh Hefner Broke Up

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  1. Thank goodness for a new post with some chicks. If I checked in one more time and saw Russel Simmons again, I;m not sure what I would have done. Thanks for all of the good work.

    By Paul R, on October 7, 2008 09:39:42

  2. So does she still get the rumored 1 million in his will when, whenever this half-dead man dies? How much does she leave with as a parting gift? He was not giving her real money, a baby, she wanted. Will she still work at Playboy as photo editor? He could not marry her because he is still married to Kimberely Conrad. How long did this woman really sleep with this guy ? I think it is gross. Sleeping with an old man like that unless you have been together for like 50 years when all , his skin, face, eardrums, di ck, were nice, firm, rock hard actually and working .
    Looks like thsiis th elast season for the show. Rightly so. Go out with a conclusion to the sl's.

    By Palo Alto, CA, on October 7, 2008 09:49:22


  3. So does she have to move out of the mansion or what?

    By anonymous, on October 7, 2008 09:49:29

  4. AAAWWWWW but but it looked like they were going to be together for ever ,is Heff runing out of gold?? did the market going down the toilet affected the old bastard so now he only has one million dollars so she is getting out of there to look for more gold somewhere else??, well men if you want a chick in her late 20's who smells like old man cum then she is your girl go for it lets see who is the desperate guy for twat that starts dating her who do you think is going to be

    By Holly is looking for new gold now, on October 7, 2008 09:51:50

  5. Inside the Playboy Mansion:

    Butler: Mr. Hefner, sir...

    Hef (relaxing as a pair of twins sucks on his shriveled dick): Yes, Jeeves

    Butler: Holly Madison has left this "Dear John" letter

    Hef (getting ready to cum): Oh, oh, shit, uh, sorry Jeeves, what does it say?

    Butler: She says she can't be with an old prune anymore.

    Hef (eyes rolling in the back of his head): Uh, uh, uh...

    Butler: I guess you don't miss her...

    Hef (cums, then shakes his head): Uh, what did you say? Oh, go get Jamie Ford, the new hardbody and move her into the house. She and the twins will be my new girlfriends...

    Butler: Yes, sir.

    By Sevenmack, on October 7, 2008 10:11:23

  6. Why do so many of you people think these relationships are real? They have never been real! These girls are hired to be 'actresses' for the Playboy mansion reality show. They all have contracts and they all get paid to pretend they're 'real' girlfriends. The people who tell the tabloids about all the 'inside' rumors are all hired to lie and create a buzz about the show too. You're all getting played.

    By anonymous, on October 7, 2008 10:14:40

  7. Is she the blonde one?

    By anonymous, on October 7, 2008 10:23:02

  8. I saw the video, I must have missed the part where she says they're split because all she does is talk about another season of the girls next door

    By anonymous, on October 7, 2008 10:44:12

  9. So, he's out of money?

    By anonymous, on October 7, 2008 11:00:41

  10. Hef is not out of money. Not even close. Holly has slept with as in has had sex with Puffin, or Puffin Boo. Read that oneline book by JillAnn Spaulding. Holly says too on the show.

    By Puffin Noooooo, on October 7, 2008 11:17:30

  11. Why would anyone read a book about this stupid show?

    By anonymous, on October 7, 2008 11:19:18

  12. Sevenmack...

    You honestly think that he can get it up? Guess you never read Bunny Tales...

    Gimme a break. He may have a bunch of tail around him, but it's more for show and companionship than sex, lets be real.

    By 789, on October 7, 2008 11:19:50

  13. 10:14 -- everyone knows Kendra likes chocolate dick, so no-one is fooled by her. Also, everyone knows Holly prime interest is money and how to spend it. As far as the remaining one, I doubt most 20 year-olds could keep up with her demands. So no -- no-one is being fooled. But perhaps you are, since you think everyone else is similarly dumb as you.

    By anonymous, on October 7, 2008 11:30:56

  14. @ anon 11:30: Anyone who cares as much as you do about these whores is dumb. They're all ugly skanks who got rich from pretending to like 80 yr. old limp dick and you're as much of a sucker as them.

    By anonymous, on October 7, 2008 11:37:14

  15. 11:37 -- oh, yes... my life *totally* revolves around these bimbos. Strange that, considering I don't even watch TV, most less own a dreaded appliance. Perhaps you ought to consider turning off the TV for a change. Your indignation over an anonymous comment demonstrates a desperate need to be heard. Posting anonymous castigations on some remote web site to an audience who can care less about your bloviating does nothing for your visibility, much less credibility, dufus.

    By anonymous, on October 7, 2008 11:48:14

  16. There are about a million fake blonds with big fake tits in LA who's do ANYTHING go be Hef's girl. There's only one Huge Hefner. Advantage: Hef.

    By thebig28, on October 7, 2008 12:00:15

  17. Um, who let the kids out of class already?

    By Fred, on October 7, 2008 12:08:37

  18. @ anon 11:30: If you never watch TV then you should spend more time in your thesaurus because your attempt at confusing people with your 25 cent words isn't working. Bill O'Reilly's word of the day has expanded your vocabulary though. Good job genius.

    By anonymous, on October 7, 2008 12:08:37

  19. ummmm break up maybe that's not the right phrase here. The old gross goat didn't die so miss plastic hit the road on to the next dolt who wants a walking talking plastic doll

    By anonymous, on October 7, 2008 12:41:41

  20. 12:08 -- do I detect envy? Yes, yes I do. Look, it wasn't I who came here and posted some idiotic message implying everyone here is an idiot. You were called on it, and in return you post a smarmy, self-important retort fit for a 7th grader. Seriously, if you are going to spar with your intellectual superiors, don't bring a knife to a gunfight, ummkay?

    By anonymous, on October 7, 2008 12:53:23

  21. Envy? No, you were called out on sounding like a 7th grader trying to sound smart, 12:53. No one envies you. You should have packed up your toys and run away a long time ago. Don't bring Hooked on Phonics to Oxford, uhmmmkaiiieyy?

    By shut up, dummy, on October 7, 2008 13:01:37

  22. We're supposed to be making fun of these dumb whores and their old millionaire pimp and the people who take this show seriously. Let's all just agree the people who spend money and too much time on this show are idiots.

    By Let's Be Friends, on October 7, 2008 13:08:08

  23. Of course he can't get it up, 789, but that's the joke. Can anyone really believe that 1) Hef will miss her and 2) that he will even fuck any of these chicks? Methinks you're reading it too literally.

    But hey, who wouldn't want to be the guy with all these whores fucking him. Yes, married life is beautiful and all; a wife will keep with you when you're sick or in trouble. But new pussy will blow your mind (and your cock) every time.

    By Sevenmack, on October 7, 2008 13:36:11

  24. 13:01 -- "You should have packed your toys and run away a long time ago" -- LOL.. you've got nothing but petulance, admit it. "Hooked on Phonics to Oxford" -- oh please, you couldn't locate Oxford on a world map. Your inability to differentiate between phonics and etymology reveals much about your education, or lack thereof. Here's a tip, you vacuous, malodorous festering heap of camel dung -- no-one cares about your celebrity histrionics. We have grown tired of your presence. Be gone.

    By anonymous, on October 7, 2008 13:49:55

  25. *sigh* I love to watch trolls fight with each other. It's more fun than doing my job.

    By anonymous, on October 7, 2008 13:51:46

  26. I would like to start a fund to sponsor the reality tv Holly's House, where she lounges about looking spectacular in her own private orphanage with 14 cute and spunky kids (plus one shy one who's a wallflower.) Little kids get a happy home, Holly gets the kiddies! Lerv ya Holly!

    By bizzybizzom, on October 7, 2008 14:29:16

  27. Mr. Crowley is in the building.

    By anonymous, on October 7, 2008 14:36:40

  28. A buck says Hef hasn't even noticed she's gone

    By I want flap-jacks!, on October 7, 2008 15:25:20

  29. This was a love story for the ages.. If these two can't make it, what hope do the rest of us have?

    By anonymous, on October 7, 2008 15:53:20

  30. This was a love story for the ages.. If these two can't make it, what hope do the rest of us have?

    By anonymous, on October 7, 2008 15:53:47

  31. UGH! Get off this website, both of you!!

    By anonymous, on October 7, 2008 16:03:52

  32. Anon 13:49:55 (and all the other fucking times you posted) --

    I don't know what gave you the impression that you're the only smart person here (or rather, why you think you're so smart in the first place). Or why you think you need to use ridiculous vocabulary in a transparent attempt to showcase your "intelligence"...
    It's a fucking celebrity gossip website. Lighten up and get off your fucking high horse.

    By Mugatu, on October 7, 2008 16:13:02

  33. I also heard that hef is broke! that at least might be a good reason for holly leaving him

    By anonymous, on October 8, 2008 02:41:37

  34. 13:49 - A friendly tip: if you're using the thesaurus in an effort to convince people that you're not retarded, I'd consider leaving the "LOL" out of your posts.

    By anonymous, on October 8, 2008 09:05:43

  35. 13:49- seriously, please, just SHUT THE FUCK UP. you are the annoying one. just fucking stop.

    By anonymous, on October 8, 2008 09:26:58

  36. That guy has pounded more tang than Neil Armstrong, I can't imagine he cares that she left

    By x24, on October 8, 2008 10:46:56

  37. Holly is a pretty girl, but the other 2, are not.
    Bridgett looks haggard and Kendra is ugly and cheap looking. But Hugh is probably looking for some younger poon. 28 is too old for him, he likes them young.

    By anonymous, on October 8, 2008 12:46:17

  38. Why does a 100-year-old guy NEED a girlfriend?

    By anonymous, on October 8, 2008 14:22:01

  39. 16:13 -- I never claimed to be intelligent (although, I would hardly question your inference). Rather, I was just pointing out your ignorance which, in retrospect, probably didn't need to be pointed out.

    09:05 -- Thanks for the friendly tip. You're the Dr. Phil of LOL. Heaven knows how silly I would look by continuing without heeding your LOL netiquette. Which begs the question: can you help me with my ROTFLMAO netiquette?

    09:26 -- Oh my! It's a verbal conflict! Although my virgin eyes can't stand the horror, I can't look away! Oh the humanity!

    (P.S. I don't use a thesaurus, but I know hard it is for double-digit IQ holders to think otherwise)

    By anonymous, on October 9, 2008 11:36:44

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