"Daddy-Long-Legs" Jerusha "Judy" Abbott was brought up at the John Grier Home, an old-fashioned orphanage. At the age of 17, Judy is informed by the asylum's dour matron that one of the trustees has offered to pay her way through college. Judy catches a glimpse of the shadow of her benefactor from the back, and knows he is a tall long-legged man. Because of this, she jokingly calls him Daddy-Long-Legs. She has an obligation to write him a monthly letter, but she will never know his identity; she must address the letters to Mr. John Smith, and he never will reply. The letters chronicles Judy's educational, personal, and social growth as she attends a "girl's college" on the East Coast. "Dear Enemy" is the sequel to novel Daddy-Long-Legs and follows the story of Sallie McBride, Judy Abbott's classmate and best friend in Daddy-Long-Legs. Dear Enemy shows how Sallie McBride grows from a frivolous socialite to a mature woman and an able executive. It also follows the development of Sallie's relationships with Gordon Hallock, a wealthy politician, and Dr. Robin MacRae, the orphanage's physician, (to whom Sallie addresses her letters: "Dear Enemy"). Both relationships are affected by Sallie's initial reluctance to commit herself to her job, and by her gradual realization of how happy the work makes her and how incomplete she'd feel without it.

Jean Webster (1876-1916) was an American writer and author of many books including Daddy-Long-Legs and Dear Enemy. Her best-known books feature lively and likeable young female protagonists who come of age intellectually, morally, and socially, but with enough humor, snappy dialogue, and gently biting social commentary to make her books palatable and enjoyable to contemporary readers.