Hugh Hefner met Mildred Williams at a party shortly after graduating from high school and the two hit it off immediately. They began dating, but their romance was cut short when Hefner had to leave for the army in 1944.
The two were able to keep in touch by writing each other letters. When Hefner returned from the army in 1946, he joined Millie at the University of Illinois. Hefner graduated in 1949 and the couple wed soon after.
But before they married, Mildred revealed she had an affair. The wedding went forward, but the shock of the betrayal haunted Hefner.
"That betrayal really shaped his view of women," Steven Watts, author of Hefner biography Mr. Playboy, said. "He loves them. He adores them, but there's that little edge of sort of keeping an eye open at the same time."