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Changing notions of marriage and family across the globe—from kinship obligation, social reproduction, and complementary labour to an ideal of marriage based on affective bonds, emotional intimacy, and pleasure—is widely read as indicating the shift from tradition to modernity. The modern companionate marriage ideal is then linked to a larger cultural transformation: the development of the modern individual self. The emergence of modern conceptions of the self in North America and Western Europe that emphasizes personal autonomy over the authority of the patriarchal family is said to have resulted in the decline of power parents and kin had over the choice of marriage partner with marriage coming to be seen as a person’s individual choice. Moreover, because companionate marriage demands a high degree of emotional and personal commitment it is generally accepted that such marriages must be entered into voluntarily, thereby recasting marriage as a contractual agreement between two people rather than an alliance between two families. Narratives about choice in marriage are, therefore, part of a historical process that emphasizes an “inner self” as integral to modern subjectivity and gives credence to individual agency in intimate relations. My thesis explores how marriage norms, family structures, and kinship relations amongst the middle-class in Sri Lanka have been transformed by social change from the early part of the twentieth century to the present. It aims to understand the ways in which modernity is reconfiguring people’s expectations of intimate relations and shaping women’s experiences and presentations of the ‘self’. In doing so, it attempts to answer three main questions: How do changing expectations of marriage structure people’s narratives about individual agency? To what extent do kinship obligations, caste considerations, and class mobility structure people’s choices in marriage? And finally, what implications do these findings have for the feminist theorization of agency and personhood? Based on fifteen months of fieldwork amongst Sinhala Buddhist middle-class families living in the city of Colombo, I argue that the urban middle-class in Sri Lanka have collectively invested in the narrative of choice through which a choosing person is consciously created as a mark of modernity and progress. However, people’s life histories show how, rather than indicating a radical shift in the way people negotiated between individual desires and social norms, the emphasis on choice signals a shift in the narrative devices used in the presentation of the self. Moreover, I argue that rather than signalling freedom, these narratives reveal how people are often burdened with the risks and responsibility of agency and grapple with making the “right” choices. By carefully deconstructing people’s anxieties that underline their narratives about choosing the right kind of partner, I reveal how choices are, in fact, structured by social norms and the expectations of family. I argue that marriage continues to be a principal strategy for social mobility and the assertion of status in contemporary Sri Lanka. Therefore, I demonstrate how caste and class considerations form the basis on which collective manoeuvring is undertaken to influence individual choices. I then argue that the trope of individual agency is not universal to all narratives about marriage and family. By examining alternative stories about marriage that defy the accepted convention I show how narratives of agency, which are deployed in certain contexts, are downplayed or denied in others; that the ‘self’, which is presented as making individual choices and actively shaping its own destiny in one context, is presented as the object of fate and circumstance in others. I conclude that because what it means to be middle-class is always a process of negotiation between competing and contradictory notions of tradition and modernity, people’s presentation of the self reveal the perpetual striving that seems to characterise modern subjectivity.