Social support is widely seen as an integral component for coping with the stresses of everyday life. While there are various sources and types of support potentially available to young people, it is perhaps less obvious the extent to which young people differentially experience these sources and types. Anecdotal evidence suggests that context, culture and other factors unique to local life shape the many dimensions of social support for youth. In this paper, we seek to examine this research need in more detail by focusing on a broad range of factors shaping youth social support and youth well-being. Drawing on mixed methods research, we examine social support evidence for adolescents in Florida, USA, and Offaly, Ireland. Through this research, we investigate how the connection between social support and well-being bears out in these two different socio-cultural contexts; second, we seek to understand whether types and sources of social support differ among youth in both countries; and what relationship exists between well-being and types and sources of support. Comparing similar measures of social support across two distinct societal contexts allows us to determine similarities and differences, while also providing suggestions for application that can shape future programmes and policy.