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Hugh Hefner and Holly Madison

Who's Dated Who feature on Hugh Hefner and Holly Madison including pictures, gossip, anniversaries, possible engagements, weddings, babies, news...

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Holly Madison

Capricorn
Hugh M. Hefner

Aries

Couple Comparison

Height

5' 7"

5' 9"

Blonde
Grey

Atheist

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Snapshot

Commenced Dating

2001

Separated

October 2008

Relationship Type

Relationship

Relationship Status

Separated

Relationship Source

whosdatedwho.com

Couple Profile

Holly Madison became one of Hugh Hefner's many girlfriends in 2001, and by 2002 she became his "#1 Girl." She stayed with him until 2008, when she told TMZ their arrangement was over.Hugh Hefner once opened up about Holly as "the one" in the Girls Of The Next Door episode.