My dissertation explores the functions of chiasmus in Henry James's works. Focusing on The Portrait of a Lady (1880-81/1908), I will argue that James uses chiasmus at phrase level to explore the boundaries between, for instance, reality and social performance (e.g."...she would be what she appeared, and she would appear what she was"). At the same time, chiastic structures at plot level steer the plot to an inevitable ending, as is the case in The Portrait of a Lady, but also in the earlier short story "The Last of the Valerii" (1878) with its ab/ba structure. In sum, I shall examine how James's use of chiasmus at these two levels can contribute to a better understanding of the ambiguities and complexities of his works and the relationships between the characters.