This work focuses on the relationship between childhood socialization, masculinities, and young men’s coming of age in contemporary Jamaica. The author elucidates social, cultural, and historical dimensions of young men’s lifeworlds and theorizes on the potential trajectories of being emotionally well and/or un-well vis-à-vis gendered normative orders of growing up and relating to others within and beyond kinship and courtship relations. Based on fieldwork, this book elaborates on the extent to which social discourses of masculinity and men’s personal experiences of their own and other men’s mental health are reproduced in Jamaica. Faulhaber places her work in contemporary psychological and medical anthropology and aims to overcome the separation of psyche, body, and environment that is often common in psychotherapy, psychiatry, and health sciences. The author embarks on this important endeavour through critical and self-reflexive ethnography and the analysis of hegemonic narratives and discourses in media and popular culture. In juxtaposition and extension to other global mental health initiatives, this work highlights that well-being, affliction and suffering can barely be grasped scientifically as objectively measurable mental states of the individual.