Relationship Details

Celebrity Biographies

Hugh Hefner dated Holly Madison in the past, but they broke up in October, 2008. Hugh Hefner dated Holly Madison for 7.8 years. Hugh Hefner is now deceased.

Hugh Hefner Profile Photo

Hugh Hefner

Media - Publisher

Why Famous: CEO of Playboy Enterprises

Age: 91 (4/9/1926 - 9/27/2017)

Hugh Hefner Photos (5)

Hugh Hefner's Relationships (31)

Holly Madison Profile Photo

Holly Madison

Entertainment - TV Personality

Why Famous: The Girls Next Door, reality show

Age: 38 (b. 12/23/1979)

Holly Madison Photos (42)

Holly Madison's Relationships (8)

Relationship Timeline

Event Start Date Length
Dating 2001 7.8 years
Broke Up 10/2008 --
 Total7.8 years

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Relationship Information, Quotes, and Trivia

Where and/or how did Hugh Hefner and Holly Madison meet?

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Why did Hugh Hefner and Holly Madison break up?

On October 7, 2008, Madison announced in a video posted on that her relationship with Hefner had ended, but that she, Bridget Marquardt, and Kendra Wilkinson are "still filming stuff together." Hugh Hefner confirmed the breakup stating that, "If Holly says it's over, I guess it's over." Hefner also confirmed that all three girls are committed to a sixth season of The Girls Next Door, and that he plans to find new live-in girlfriends.

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Classic Quotes by Hugh Hefner and Holly Madison about their relationship:

"There will certainly be a lot of romantic years ahead, but a wedding we will see." Hugh Hefner 2/4/2008
"We are just going out to dinner. I am trying to think of something creative, but at this point I am just going to save all of my ideas for Christmas 'cause Valentine's Day came up fast." Holly Madison 2/4/2008
"I haven't had sex in a really long time. It might be refreshing to date someone who is not high-maintenance." Holly Madison 11/24/2008
"Living with Hef brought down my self-esteem a lot. You have to look a certain way at the mansion. If you look at Hef's girlfriend now, she basically looks like aclone of me." Holly Madison
"Over the course of my life I've had more than my fair share of romantic relationships with wonderful women. Many moved on to live happy, healthy and productive lives and I'm pleased to say remain dear friends today. Sadly, there are a few who have chosen to rewrite history in an attempt to stay in the spotlight. I guess, as the old saying goes: You can't win 'em all." Hugh Hefner 6/2015
"Everyone thinks that the infamous metal gate was meant to keep people out. But I grew to feel it was meant to lock me in. Maybe it was the pot and the alcohol, but drowning myself seemed like the logical way to escape the ridiculous life I was leading. Would he even miss me? No, I was certain I was just another warm body as we all were." Holly Madison 6/2015

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