Middle of the Night(1959)

Overview:

Jerry Kingsley is a wealthy garment manufacturer left lonely in his 50s when his wife dies. Despite the difference in their ages, he strikes up a romance with divorced 24-year-old receptionist Betty. The relationship is dismissed by his daughter, Lillian, discouraged by his sister, Evelyn, and denounced by Betty's mother. But when Jerry begins to mention marriage, even Betty is forced to confront her ambivalence.