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!

1 of 15

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

2 of 15

Hugh Hefner & Sondra Theodore

Hugh Hefner & Sondra Theodore

3 of 15

Mildred ‘Millie’ Williams

Mildred ‘Millie’ Williams

4 of 15

Hugh Hefner & Barbi Benton

Hugh Hefner & Barbi Benton

5 of 15

Shannon Tweed

Shannon Tweed

6 of 15

Hugh Hefner & Carrie Leigh

Hugh Hefner & Carrie Leigh

7 of 15

Hugh Hefner & Kimberley Conrad

Hugh Hefner & Kimberley Conrad

8 of 15

Hugh Hefner With Mandy & Sandy Bentley

Hugh Hefner With Mandy & Sandy Bentley

9 of 15

Hugh Hefner & Brande Roderick

Hugh Hefner & Brande Roderick

10 of 15

Izabella St. James

Izabella St. James

11 of 15

Hugh Hefner & Holly Madison

Hugh Hefner & Holly Madison

12 of 15

Hugh Hefner & Bridget Marquardt

Hugh Hefner & Bridget Marquardt

13 of 15

Hugh Hefner & Kendra Wilkinson

Hugh Hefner & Kendra Wilkinson

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Hugh Hefner With Kristina & Karissa Shannon

Hugh Hefner With Kristina & Karissa Shannon

15 of 15

Hugh Hefner & Crystal Harris

Hugh Hefner & Crystal Harris
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