In recent years, Indian TV screens have seen a proliferation of reality shows focused on romance and dating. This essay examines a range of dating formats arguing that such shows offer rich insights into the ways in which contemporary Indian media culture is negotiating and promoting models of gendered individualism and ‘enterprising’ modes of selfhood. Drawing upon data from a study funded by the Australian Research Council on lifestyle and reality TV in South East Asia, our analysis focuses on the complex relationship between the ideals of aspirational modernity and choice-based selfhood promoted by these shows and the realities of ongoing gendered social and economic inequities and the continued cultural potency of religious and familial notions of duty.