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Hugh Hefner and Holly Madison

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Hugh Hefner and Holly Madison

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Commenced Dating
2001
Separated
October 2008
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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.

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