How He Was on Dates
When it came to going on dates, Sinatra loved driving his ladies around himself (instead of a chauffeur). He purposely never drove Actress Angie Dickinson, one of his many girlfriends, around in a convertible because he knew she didn’t want her hair to get messed up. And when it came to dancing, according to his second wife Ava Gardner, “He was hopeless on the dance floor.”
Frank Sinatra and Angie Dickinson in the film “Ocean’s Eleven,” 1960. Photo by Bettmann / Contributor / Getty Images
Although his list of women, as you’ll see, is filled with beauties, he didn’t like women who tried too hard. There was one time when, out of curiosity, Sinatra went to Hugh Hefner’s Playboy Club in Chicago. He reportedly said that he thought the girls tried too hard. He even skipped out on the festivities and went back to his room at the Ambassador Hotel.