Middle of the Night (1959)

For every girl who was ever involved with an older man!

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.