From the perspective of psychotherapists involved in working with young men, it is particularly interesting to consider ways in which boys may construct versions of their masculinities through an amalgam of social and personal discourses. Amongst the issues relating to young masculinities to arise systematically in research studies and in psychotherapeutic work, two are of particular interest for emerging understanding of the emotional consequences of new structures of masculine identities. These are the relationship boys have with their fathers, and the impact of social discourses on homosexuality. In this paper, material is presented from one boy who participated in an in-depth interview study of boys in London secondary schools. This boy reveals in unusual detail the ways in which dominant discourses on being ‘gay’ and on fathers govern the construction of contemporary young masculinities, even when boys themselves seek to resist these discourses. It is suggested that consideration of the operation of these discourses in young people's lives is a relevant concern for psychotherapists.