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The shift to companionate marriage in South Asia and elsewhere is widely read as a move from ‘tradition’ to ‘modernity’ resulting in an expansion of individual agency, especially for women. This paper critically examines the narratives of urban middle-class women in Sri Lanka spanning three generations to illustrate that rather than indicating a radical shift in the way they 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’. The paper illustrates how young women’s narratives about marriage appear to suggest ‘modernity’ as inevitable—that its processes are reconstituting the person who, less constrained by ‘tradition’ and collective expectations, is now experiencing greater freedom in the domain of marriage. However, it also shows how urban middle-class families in Sri Lanka have collectively invested in the narrative of choice through which ‘a choosing person’ is consciously created as a mark of the family’s modernity and progress. Rather than signalling freedom, these narratives about choice reveal how women are often burdened with the risks and responsibility of agency. The paper illustrates that the ‘choosing person’ is produced through narratives that emphasise agency as a responsibility that must be exercised with caution because women are expected by and obligated to their families to make the ‘right’ choices. Hence, a closer look at the individualised ‘choosing person’ reveals a less unitary, relational self with permeable boundaries embedded within and accountable to family and kinship.