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?
"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?
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