Hugh Hefner’s Wives and Girlfriends Through the Years (Photos)

Hugh Hefner passed away Wednesday at 91-years-old and he sure did live a life fit for the founder of Playboy Enterprises.

Here are some of the wives and girlfriends of Hefner’s past. 

Mildred Williams (1949-1959) 

Hefner met Mildred Williams in college and they got married in 1949. The pair had two kids together. Williams had revealed that she had an affair while Hefner was serving in the army. He’s said: “That was the most devastating moment in my life.”

According to Hefner, his wife would let him sleep with other women to make up for her infidelity.