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.

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