Fictional narratives on Chennai, after its official conversion from Madras in 1996, offer an intriguing register for exploring ways of belonging. Using a postcolonial framework, the paper closely scrutinizes T. S. Tirumurti’s Clive Avenue and Chennaivaasi (and some other authors invested in Chennai’s contemporary culture) and subjects them to critique as sites of meaning making. An effort is made to explore how these narratives respond to the new reality of Chennai, to what extent they see the city producing a standardized experience, and how the fictional characters corroborate or contest institutional change. In the process, the texts are brought to converse with the postcolonial desire for cultural autonomy, its mediation by a nativist agenda, as well as the ambivalence and contradictions inherent in such a desire. The texts betray the inadequacies of the new name as a stable container of cultural meanings and propose an idea of the city that is internally incoherent and multi-experiential.