Singapore is a nation of paradoxes. Renowned for its rapid economic transformation from third world to first, Singapore’s global city aspirations necessitate a forward-looking and cosmopolitan approach to development. Yet, the state continues to maintain a conservative, moralistic stance on deviant subjectivities. This ideological ambivalence is exemplified in the state’s approach to public housing, where housing policy works to strengthen Singapore’s position on the global economic stage by fostering a stable, procreative labor force, yet also safeguard its national fabric from erosive globalizing influences by preserving “the family”. Peeling back the layers of state rhetoric and justification, I contend that there exists a triangular relationship between housing policy, kinship relations, and state power, in which the state uses housing policy to construct narratives of the “heartland” and imagined citizen. Finally, I explore the converse relationship - how citizens see themselves and their relationship to the state. Through a close reading of selected poems and short stories by prominent local writer Alfian Sa’at, I uncover spaces for negotiation and resistance in response to the social engineering of the government. I argue that literature provides a crucial voice for the voiceless in Singapore, shattering the state’s notion of the ideal national subject and intimating the possibility for disidentification and self-definition.