Letters to Hef, His Fiancee, and Holly Who Got Away

From: usweekly.com

Dear Hef,

Congratulations! You’re getting married! You must be overwhlemed with joy! This is an exciting event in the life of a young ma-. Oh. Right. Not young. But it’s still exciting! Marriage isn’t the province of the young, after all, and even 84 year old men are entitled to new adventures.With 24 year old women. Who are not their grand-daughters but could be.

Now, has anyone sat you down and explained about the Birds and the Bees to you in advance of your wedding night? What’s that? You already know about the Birds and the Bees? You’ve been Bee-ing Birds for over 70 years? You actually ARE the original Bee? Oh. Gotcha.

Well, ok, then, you know what you’re doing. But you should remember that not all women look like the altered specimens in men’s magazines. You need to expect imperfections and flaws and – What’s that? You created those kind of women? You have an endless supply of them on tap? You finance their transformation from pretty girl to artificially perfect girl? Your fiancee is one of them? Oh. Ok.

Well, you do know that marriage is a lifetime commitment that comes with a presumption of fidelity and mutual respect and clearly shared expectations of behaviors and – what’s that? This is your third marriage and you didn’t bother with those other things before? And yet your second wife stayed married to you for over 20 years even though you were estranged and living separate lives in separate homes for most of that time? And you had multiple girlfriends at any given time? Oh.

Well, then I guess you’ve got it all covered. You created the babe, you’ve got her surgeon on speed dial in case something on her body starts to show age, and you have no compunctions about cheating or divorcing or both. Best of luck to you!

Confused about your appeal,



Dear Crystal Harris,

So. Hef proposed. You win?

Sweetie, you don’t seem like a dumb girl. And I’m willing to concede that you know things about Hef’s character that I’ll never be privy to. But really? This is the horse you think your wagon should be hitched to? An 84 year old man who has made a fortune objectifying women?

I’m sure he makes you feel pretty. Pretty is his stock in trade. Pretty, young, and somewhat naive are what he sells. Big-eyed beauties who toss their hair for the camera and seem somehow unaware that they’re stark naked when the flash goes off. He goes in search of these girls by the score and where he can’t find them, he creates them by subsidizing plastic surgery for the lucky few he selects as his own. You’re one in a long string of girls that he’s bedded or wedded.

Do you think you’ll be the last?

Listen Crystal, if you’re down with all the Hef-related baggage and want to be an eternal pin-up, good on ya. But you’re still so young and sheltered that The Little Mermaid is your favorite movie. You’ve spent a significant part of your adult life living under the patronage of Hef. You have options that you don’t even know about. If I were your BFF, I’d say you take a good look at them before you say “I Do”. But that’s just me. I’m all wacky and weird and into female empowerment and individuality instead of being one of a herd of altered blondes sucking up to a guy with a magazine.

I wish you a long and happy marriage. Or at least a happy one for as long as Hef shall live.




Dear Holly Madison,

GIRL! You are so lucky to have gotten out. Bottles up, babe! Drink to a life without Hef and the Playboy Bunny Borg he keeps in the mansion!

Party on!


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18 comments for “Letters to Hef, His Fiancee, and Holly Who Got Away

  1. KLZ
    January 11, 2011 at 10:11 am

    Easy – she thinks he’s going to die.

    I’ll bet all his money goes to his daughter, the company or a plastic surgeon though. Jokes on her…

  2. TheNextMartha
    January 11, 2011 at 11:01 am

    So you don’t think Hef would jump at the chance to have Holly AND Crystal in the sack?

  3. Rebekah @ Mom-In-A-Million
    January 11, 2011 at 12:16 pm

    @TheNextMartha, what makes you think he hasn’t already done that?

  4. January 11, 2011 at 12:20 pm

    This is, by far and away, my FAVORITE post of the day. I should just hire you to write letters FOR me. 😉

  5. January 11, 2011 at 12:25 pm

    I’m making that clicking sound w my tongue… I’m not judging anyone or anything… I just find it all very….. Interesting….

  6. Erica Snipes
    January 11, 2011 at 12:40 pm

    The most important people Hef has in his life are his attorneys that we never hear about. You know, the ones that advise him how to protect his money from the most recent wife that naively thinks she’s going to get a piece of it when Hef finally has that sex induced heart attack that does him in. Sorry, was that out loud?! Hmmm. As the recent comment says…very….interesting…

  7. January 11, 2011 at 3:19 pm

    Oh she won’t get much that is for sure. Think about it – Playboy is PRINT media with a little digital clacked on because they had to move with the times. Its not just Hef that is old. http://money.cnn.com/2011/01/10/news/companies/playboy_hefner/index.htm

  8. January 11, 2011 at 3:51 pm

    I believe you’re just jealous that you’re not a blond gym goddess getting shagged by an 84 year old millionaire. I know you’re angry that you won’t get the chance of having your grandfather-figure stroking out while on top of you, making sweet, sweet love to you.

    And, I have to say, jealousy is such an ugly color on you, love. 😀

    Brb, even typing that emotionally scarring image made me throw up a bit in my mouth.

  9. amy
    January 11, 2011 at 4:04 pm

    LOL Loved the letters.
    Do remember in the movie “Monster-in-Law” when Jane Fonda is interviewing the singer and she asked what were her favorite movies and she says the old ones…like “Little Mermaid” and seeing that Hef’s fiancee loves that movie I wonder if she ever gets out in the real world.
    So, do you think that they know that they are the butt of every comics punchline? I wonder how much Viagra Hef has to use to keep up with his little bunny? HMMM

  10. January 11, 2011 at 6:08 pm

    Love, Love, Love this!

  11. January 11, 2011 at 8:59 pm


  12. January 12, 2011 at 12:49 pm

    Hef just took Playboy private again. It used to be a publicly traded stock, but he bought up all the shares, and took the corporation private again.

    Playboy Enterprises isn’t what it used to be. He’s trying desperately to hold on to a magazine/enterprise that is being put out of business by the internet.

    But I guess the new Fiancee isn’t a business major.

  13. January 14, 2011 at 4:39 pm

    I read the announcement of Hef’s engagement and I gasped–“poor Holly!” like some insane person. Thank you for putting this all in perspective for me. What’s Hugh Hefner’s deal and why do we just not question every weird quirk that he shares with the world? The Girls Next Door is kind of like making a warm and fuzzy cartoon version of The Accused. OK, maybe that’s not an appropriate analogy. I just don’t understand how a feminist like myself could be caught so off guard by the packaging of Hugh Hefner and The Girls Next Door that I would lose all perspective on what it means when an 80 year old man proposes to a 20 year old woman.

  14. Brigitte
    February 25, 2011 at 1:50 am

    OMG … Kadield … you had to go there? eeewww, i almost threw up for real reading that. Oh great, now I have to disinfect my brain & I feel like taking a shower. in bleach.

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