He Did It His Way: All the (Many) Women in Frank Sinatra’s Life

What He Looked for in a Woman

First, let’s ask ourselves, what did Frank Sinatra look for in a woman? Well, he once answered that very question with “A sense of humor.” He then added: “I’m supposed to have a Ph.D. on the subject of women, but the truth is, I’ve flunked more often than not. I’m very fond of women; I admire them. But like all men, I don’t understand them.”

Frank Sinatra and Kathryn Grayson wearing a bridal gown and a suit while holding hands in a scene from the film The Kissing Bandit.”

Frank Sinatra and Kathryn Grayson in a scene from the film “The Kissing Bandit” 1948. Photo by FilmPublicityArchive/United Archives/Getty Images

Sinatra once said that the first thing he noticed about a woman was her hands. “How they’re kept,” to be exact. “Grooming is important.” He also said that he doesn’t like “excessive makeup.” According to his former valet George Jacobs, the singer “craved class.” He also hated women who smoked excessively.