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In the early years of the twentieth century, Shaw had an intriguing relationship with Erica May Cotterill, one that influenced the creation of characters and the themes of two plays around the end of the Edwardian era, Misalliance and Fanny’s First Play, and of Heartbreak House, written World War I. This article presents a new exploration of the Shaw–Cotterill relationship and of Shaw’s experiences of and attitudes towards sex. This account of Shaw’s sexually involved relationships combats a persistent legend about his sexuality, that he was “bloodless, asexual vegetarian.” Shaw had a passionate self, but as Cotterill maintained he also had conflicted feelings about sex and about his own desires. Although he made very positive statements about the importance of sex, he also seems to have seen sexual feelings and experiences as being somehow separate from the individualizing, distinctive features of human personality.