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Holly to Hugh: Hef Off

10/7/2008 8:06 AM PDT BY TMZ STAFF

Holly Madison dropped some big news on us Monday night -- she and Hef are no longer together.
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If a love affair between a 28-year-old woman and an 82-year-old man can't work, what hope is there for the rest of us?


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At Hef's age he probley forgot he ever dated her by now.Holly is over the hill for that old fart.


2171 days ago

You're Killing Me Larry    

Wow: Holly is "breaking up" with the octogenarian stud coincidentally with shares of Playboy Enterprises falling to $3.04 on the NYSE and panic setting in as to how to stem the financial bleed and generate more cash to keep the mansion afloat. Could it just be possible that the multiple girlfriends on Hef's arm were a contrived charade for "The Girl's Next Door?" After all, the Playboy lifestyle is predicated on the myth that Hugh Hefner is jetting around the globe with any number of available nubile young women at his disposal.

It sells a lot more magazines than picturing an 82 year-old man going to bed early with a bowl of chicken soup and watching old movies on TV.

2171 days ago


I love you Holly, you will be a great success in life. You are too good to stay with someone who won't give you what you want. You are beautiful inside and out. I can't wait to see what you do next!

2171 days ago


I like Holly. You people are mean. But where kan i see an old photo of her??

2171 days ago


Holly, 28! PLEASE!

2171 days ago


I agree about Bridget being a total sweetheart and being the only real one of the 3. Kendra has her moments, but she is just young and gotten her way too much in life to have any substance. If it is true, it's no surprise! I have always tried to decide if Holly's facial expressions were limited to a smile and a blank look...never see her face move in any other way. Botox? Even on really joyous occasions like her sister getting married, it was the same. When she made that slip and slide, even going down that her face remained the same as if she was smiling for a picture! She just gives off a real snarky vibe all the time. Hef seems to truly care about all of them, but only in the most grandfatherly way (well and for sex too). I don't feel bad for any of them, they have been living a very lavish lifestyle! All of the posing for pictures in the mansion and a party a week has turned them all into cardboard cut outs. Hef, keep on doing what you do. Holly was/is silly to think he would ever marry her! I think he truly enjoys the company of the three of them- but c'mon, no way he will ever settle down and pop the question. Kendra should go off and do something meaningful, Bridget should get her own campy show on Bravo/ or E! or be an entertainment journalist, and Holly should learn to crack a real smile and open up her own "men's magazine".

2171 days ago

Boston Kate    

I think Holly will be just fine. I think she's actually intelligent. What fun it must be/have been living at the Mansion. If these girls did their homework, before being involved with the Heffner/Playboy machine, they feel/lfelt lucky to be a part of it. In his prime, Hefner was admired by men and loved by women. He is an icon. Do any, of you from Boston, remember there used to be a Playboy Club in Park Square? Bridget, you'd look younger, if you cut your hair. You looked fabulous in your birthday/Murder Mystery birthday show.

2171 days ago


I never liked that catty snooty baggage. She wanted to hook Hef so bad......and now she's out. Could not happen to a better person.

2171 days ago


To borrow from an old joke, Now that we have established what you are, what will be the price for the next guy to sample your body? My guess is she should pay the first few guys as she has to be out of sexual shape and rusty.

2171 days ago


AWWW. Poor Holly and poor Puffin Boooooo....

Whatevs. I'm so addicted to TGND, it's crazy. I love watching people act like complete idiots. It gives me something to laugh about.

2171 days ago

the short chick in the back    


Hef called into Ryan Seacrest's radio show this weekend & sd that they were still together.

He did go on to say that because Holly wanted to marriage & children it was understandable that they might part ways eventually, but... sounds like he thinks theyre still on as of this wknd.

2171 days ago


I know Holly and Hef and I'm thrilled that Hef decided it was over with. The girl is a ungreatful piece of crap. She all of a sudden thought she was all unique and special and filled her own head with an ego trip. Hef doesn't have an ego and he is the one making all this wonderful money. Holly on the other hand got her head really high up her ass and I think in the long run, Hef finally saw it and decided that...especially her wanting a baby so bad..what a ridiculous thing. Then Hef would owe her lots of money, things would get legally complicated and being 81 yrs old, Hef doesn't need that in his life. He does love Kim who lives next door and Holly knew it in her heart..Who cares about Holly.

2171 days ago

Bob Booie    

she mustve got tired of changing his diaper

2171 days ago

Jennifa O Jenny    

Good thing she got out of the relationship with Hef - he was never going to marry her or have a baby with her, which is what she wanted. Hey, she has her own money now and probably still works at his magazine - so she is set! Now she can find a guy who is willing to give her the family she's been wanting.

2171 days ago


I liked Bridget

Holly, aside from being the least attractive, you could tell was just out for money
Kenra, while probably being the best looking, is as dumb as a doorknob..could you imagine a life with her? Talk about daily aggravation.

Bridget was the brighest, good looking, really pretty normal...she'll come out of all of this the best.

2171 days ago
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