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James’s novel is widely interpreted as a devastating critique of the early women’s rights movement in America. At the time the Bostonians was written, the advancement of women’s rights was in crisis: dismayed by the failure to secure women’s suffrage along with that of freed black men after the Civil War, advocates split into separate organizations. Postwar emancipation also experienced dramatic setbacks as Jim Crow Laws became further entrenched in the South, and the North turned its attention inward, focusing on rapid economic expansion. Within the women’s rights movement, the personal was truly political: the split between the groups placed considerable stress on the deep friendships enjoyed by many advocates, as they were effectively forced to choose between a gradualist approach to enacting women’s suffrage that may not be successful, on the one hand, and the potential alienation of freed black men (and many freed black women), on the other. I explore the underlying theme of love and friendship throughout the novel, which reflects opportunities lost, paths not taken, possibilities not explored. I conclude that James was a more sympathetic critic of the early women’s rights movement than interpreters have claimed, at once admiring its successes while acknowledging the tragic difficulties that lay ahead.