In 1975, twenty-one-year-old Dvorah Telushkin wrote a letter to the great Yiddish writer Isaac Bashevis Singer, offering to drive him to and from a creative writing class in return for permission to attend the course. The literary master, then seventy-one, accepted the offer, which led to a twelve-year-long apprenticeship for Telushkin.

Throughout Dvorah Telushkin's tenure with Singer, she kept detailed diaries chronicling both their literary efforts and the evolution of their personal relationship. Indeed, Telushkin was the one person to whom Singer tried to teach his craft as a...