In attempts to arrest the chronic declined of fertility rates, governments in East Asia and Singapore have introduced pro-family packages with generous fiscal incentives to attract married couples to grow larger families. This paper looks at the case of Singapore where pro-natalist policies were introduced since mid 1980s, and which were enhanced most recently in 2008. The incentives cover an expansive range of benefits from fiscal incentives which include the iconic Baby Bonus schemes, to various childcare support and leave options, the most generous being a 16-week paid maternity leave for mothers, to housing priorities. Yet, the total fertility rate in this small nation state remains at critically low levels. Do such pro-family policies really work? To assess the role of such initiatives, we look at both short-term gains and long-term effects. The paper concludes that pro-natalist incentives tend to speak mainly to converts as they do not address root causes of low fertility. Therefore, impact on total fertility rate year-on-year will be modest. However, the more significant impact of pro-family policies is the long-term effect on ideological shifts. Sustained efforts by the state to promote family work will eventually reposition the family to a dominant status in the face of contesting ideologies.