There is a well-established body of evidence that intergenerational bonding programs (IGPs) can improve the overall well-being of older adults and strengthen relationships and understanding between generations. There is limited literature on the experience of IGPs in an Asian context, despite many of these countries facing faster rates of population ageing than other Western countries. In Singapore, intergenerational bonding is a priority in national efforts to encourage successful ageing. This paper presents a case study of the development and implementation of a co-located (shared site) model IGP in Singapore. Drawing on interviews with key stakeholders, the aim of this case study is to present the realities of the evolution of an IGP from conceptualisation through to implementation, and used the nursing home’s COVID-19 experience to illustrate issues of sustainability affecting IGPs with vulnerable populations. The findings will inform the development and implementation of similar future programs.