Jerusha Abbott, an eighteen year old orphan, faces an uncertain future in the charity home where she has lived all her life. On reaching adulthood, the orphanage can no longer offer shelter to its inmates. Her anxiety leads her into wild speculation when she is summoned to the matron's office. But a surprise awaits her. One of the visitors, a wealthy Trustee of the orphanage, has offered to fund Jerusha's college education and fulfill her dreams of becoming a writer. The only condition he makes is that he remain anonymous and that she write to him regularly about her progress...

Dear Enemy is the sequel to Jean Webster’s novel Daddy-Long-Legs. The story as presented in a series of letters written by Sallie McBride, Judy Abbott’s college mate in Daddy-Long-Legs. Among the recipients of the letters are the president of the orphanage where Sallie is filling in until a new director can be installed, his wife (Judy Abbott of Daddy-Long-Legs), and the orphanage’s doctor (to whom Sallie addresses her letters: “Dear Enemy”).