Much of Singapore’s recent problems with social acceptance and integration of foreigners is attributed to the city-state's sustained ultra-low fertility. To augment labour shortage, state policies on immigrant were eased to facilitate an inflow of guest workers. The backlash on rapid globalisation of the workforce was felt acutely when the non-resident segment rose to account for over 20% of the almost 5.2 million population. To ease social tension between locals and foreigners, the city-state has to curb reliance on foreign labour through ensuring a steady growth of the local population. This paper discusses the social, cultural and structural barriers to fertility growth. The discourse highlights limitations of poor work-life integration as well as over-demands on parenting. Radical transformations that target macro structures are proposed to return to centre the social institution of the family. The proposals hope to affect a better work-life balance and reconceptualise responsible parenting so that singles have sufficient resources to invest in marriage, and family formation becomes a more achievable life goal for Singaporeans.