Frank Sinatra and Grace Kelly

Though his love life was hardly a secret, during the Gardner saga Frank issued what the press dubbed “Sinatra’s law,” an edict that held that his private affairs were off-limits. In late 1954, he made a play for Grace Kelly. Though involved with another man, and in spite of the lasting friendship she had forged with Ava, she agreed to see him. Their date reportedly went badly, in part because he was already drunk when he picked her up, in part because he spent a good deal of the evening weeping about Ava. “He held no attraction for her,” said Celeste Holm, who later worked with them both on the movie High Society. “Grace regarded Frank as a street kid . . . She was on a different level. She was a princess long before she married Prince Rainier.”