Cultural scholars are paying increasing attention to the ways in which choice has become a cultural obligation deeply ingrained in neoliberal, post-feminist, therapeutic and consumerist norms. Drawing insights from this literature, this paper first charts the changing discourse on choice, and then goes on to both examine and challenge the centrality of the rhetoric of choice in contemporary discourses of singlehood and single women. In my analysis, the idea of choice is posited as a multivalent signifier dependent on changing social contexts and denoting shifting aspects of feminine subjectivity and personal relations. It is my aim thereby to problematize notions of choice and singlehood, as well as to question the cultural processes that produce them. To do so, I probe the discursive relations that produce distinctive clusters of meanings, as well as the tensions and contradictions that emerge around them. Such a reading emerges from a content-based analysis of readers' comments and responses to an online Internet column depicting the various advantages of being ‘single-by-choice’. The findings show that while choice can be a discursive force that enables single women to resist traditional family forms and establish their chosen subjectivities, the centrality of choice in the construction of intimate relations today also casts in doubt and paradoxically delegitimizes single women's option of autonomy and individuality. Some of the social interpretations of choice denote that single women are endowed with a partial and incomplete subjectivity, while according to other stances the choice of singlehood signifies a radical option for claiming singlehood as a long-term way of life. However, the aim of the critique proposed here is not merely to deconstruct the discursive mechanism that delegitimizes singlehood, but also to point out some of the potential limitations emerging from the new counter-discourse of chosen singlehood.