Holly Madison on Hugh Hefner Engagement: Mixed, Complicated Feelings

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In 2008, Holly Madison was the busty blonde rumored to be marrying Hugh Hefner.

Fast forward a couple years, though, and Crystal Harris is the young model engaged to the Playboy founder. How did Madison react to that news when she found out?

Holly Madison Pic
Hef's Ex-Fiancee

"I [was] very surprised," Holly tells E! News. "I have a lot of different feelings on it. I don't just feel one way. I kind of didn't want to put a generic statement out there like 'Congratulations!' because I felt everyone would see through that."

So, what did Madison do? She visited Hef and Harris at the Playboy Mansion this week - with cameras from her reality show in tow, of course.

"I wanted to see him and Crystal and tell everybody face-to-face how I felt. It went very well," she said. "I had a good day."

But did Hefner make a good choice? Who would you rather give it to for the rest of your life?


Elle sont canons


Agree Jennifer M.! I dont' think he would know what love is, if he doesn't at this point, when?? Oh yea on his freaking death bed when no one will be there.

Jennifer miller

What goes around comes around. Holly should not be mad. Hefner is a dog and will probably never be happy with whoever he is with.


Well, i guess this goes to show that men truly are fickle. It seems that Holly really loved the man but he obviously didn't truly love her. As we can all see by his actions of formalizing his engagement with the next blonde he took in after breaking it off with Holly a while back.


The only one on this planet that couldn't figure out that there can only be one alpha dog in the mansion way Holly. Lesson learned?


Just to show that he is demented huh Mandy?


If Hef wants to make the world still think he's got it marry a 70+ year old woman. That would be a truly happy ending. In a recent interview he states that his long time secretary is the wonder of his life. Hello Hef! The wonder of your life is your soulmate!


HAHA I can't stop laughing!! She's jealous of a younger version of her, yeah no wonder!! Get use to it, their will always be a younger hotter version. That is why you need to have more than just your pretty face a big FAKE boobs to get through life LMFAO

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Holly Madison Biography

Holly Madison Photograph
Holly Madison is a Playboy model and the ex-girlfriend of Hugh Hefner. As for Madison, she is best known for getting naked a lot and... More »
Astoria, Oregon
Full Name
Holly Cullen

Holly Madison Quotes

We are no closer to getting married than we were years ago. It's like a car stalled at the side of the road.

Holly Madison [on Hugh Hefner]

I have no pull anymore. Hef and I aren't together.

Holly Madison