Why Holly Madison Ended Her Relationship with Hugh Hefner

Season 5 Episode 510
Aired on 09/26/2015 | CC tv-14
Holly Madison rose to fame in 2005 as Playboy founder Hugh Hefner's number one girlfriend on the E! reality series The Girls Next Door. For years, cameras documented the seemingly glamorous life of Hugh, Holly and Hugh's other live-in girlfriends, Bridget Marquardt and Kendra Wilkinson.

Then, in 2009, Holly says she hit a rocky patch with Hugh when it became clear that Bridget and Kendra were leaving the Playboy Mansion and moving on to new things. "I just had enough. I had realized all the delusions I'd been under and that this was no longer the life for me," she says. "The whole thing kind of came to a bizarre peak when I went into Hef's room to pack up the remainder of my things, and I found on my side of the bed a folder that he left out."

Holly says the folder contained a copy of Hugh's will, which indicated that he was planning to leave her $3 million. "It was very clear to me that he left that out for me to see because he was hoping it would change my mind and get me to stay," she says. "It just kind of disgusted me more than anything."

In the above clip, watch as Holly talks candidly about her break up with Hugh.

Watch more from Holly Madison on Oprah: Where Are They Now?, airing Saturday nights at 10/9c on OWN.