ince the latter part of the twentieth century there has been increasing recognition of the need for more effective approaches to engaging adolescent boys. Much of the focus in youth work practice and research has previously been dominated by attempts to better understand young male bio-social and cognitive development through examining high risk issues such as offending, violence, substance use, anti-social behaviour and mental health. The recent interest in critical studies of masculinities have further highlighted complex and contradictory ways in which traditional notions of becoming a man impact, often negatively, upon male behaviour and development. Despite increased awareness and concern about adolescent male development, practitioners across various professions frequently report finding it difficult to engage positively with certain young men and admit to lacking the confidence and skills to develop meaningful practice. This paper draws upon thirty years’ experience of youth work practice and social research carried out by the authors with adolescent boys within a divided and contested political context. However, while the article draws upon local research findings and practice experiences from Northern Ireland, we believe the learning will be of value to educators and practitioners working with adolescent boys in other societies and contexts.