This article explores the stories of single women living in the urban metropolis of Kolkata, and in smaller towns and villages of West Bengal, as a means to illuminate emerging possibilities and constraints of selfhood for women in contemporary India. In so doing, the piece examines the ways gendered identities intersect with other forces and ideals at stake, including the institution of heterosexual marriage, class mobilities, and values surrounding individualist versus relational personhood. Because they are positioned outside the norm, those who live singly offer an unusually insightful perspective on their wider society's values and institutions. In these ways, the narratives of three single women and others each illuminate their tellers’ intricate subjectivities as well as offer broader social‐cultural critique. Their stories reveal the ambiguity, painful consequences, and sometimes hopefulness surrounding the “choice” to be single for women and suggest that social recognition and belonging are even more important than independence and true singlehood in the lives of those who live outside marriage in India. [belonging, class, gender, self, sexuality, marriage]