All His Wives & Girlfriends – Hollywood Life

Between his three wives and many girlfriends, Hugh Hefner had no shortage of lady love during his 91 years. Here are the women he married and dated over the years!

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Hugh Hefner’s Partners: All Of The ‘Playboy’ Creator’s Wives & Girlfriends Through The Years

Hugh Hefner’s Partners: All Of The ‘Playboy’ Creator’s Wives & Girlfriends Through The Years

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Hugh Hefner & Sondra Theodore

Hugh Hefner & Sondra Theodore

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Mildred ‘Millie’ Williams

Mildred ‘Millie’ Williams

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Hugh Hefner & Barbi Benton

Hugh Hefner & Barbi Benton

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Shannon Tweed

Shannon Tweed

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Hugh Hefner & Carrie Leigh

Hugh Hefner & Carrie Leigh

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Hugh Hefner & Kimberley Conrad

Hugh Hefner & Kimberley Conrad

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Hugh Hefner With Mandy & Sandy Bentley

Hugh Hefner With Mandy & Sandy Bentley

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Hugh Hefner & Brande Roderick

Hugh Hefner & Brande Roderick

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Izabella St. James

Izabella St. James

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Hugh Hefner & Holly Madison

Hugh Hefner & Holly Madison

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Hugh Hefner & Bridget Marquardt

Hugh Hefner & Bridget Marquardt

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Hugh Hefner & Kendra Wilkinson

Hugh Hefner & Kendra Wilkinson

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Hugh Hefner With Kristina & Karissa Shannon

Hugh Hefner With Kristina & Karissa Shannon

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Hugh Hefner & Crystal Harris

Hugh Hefner & Crystal Harris
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