Indecisive heiress Dee Dee Dillwood is pushed into marrying her sixth fiancée, but unable to face the wedding night, she flees into the adjacent hotel room of commercial pilot Marvin Payne, who just wants to sleep. She then persuades him to take her to California.

Penny Addams lives in a constant state of depression stemming from the trauma of her father's death when she was just a young girl. Her brother, Chase, and stepmother, Lee, work to help Penny process her grief through psychotherapy and revisiting their past, but only the revelation of long-buried family secrets -- including her mother's secret lover and the true nature of her father's death -- can bring Penny out of her intense despair.

Pickpocket Kitty's life changes when painter Thomas Gainsborough makes her portrait. The artwork gains the attention of Sir Hugh Marcy, who later decides to use her for his benefit.