This study is concerned with how boys grow to be men and the subject positions which the secondary school curriculum constructs, supports, and invites boys to take up. Thirty predominantly Pakeha, high achieving boys from a fifth form class in a single-sex school participated. Two boys in particular were focused on throughout a series of mathematics and English lessons. Using a generative methodology, I investigated and illuminated curriculum enactment as it pertained to the lived realities of these boys. This study supports previous studies which have uncovered the androcentric nature of the school curriculum. It also reveals the contradictory and conflicting subject positions embedded in curriculum enactment in the classroom. The processes of negotiating and mediating these subject positions in the formation of a personal 'sense of self' are complex and involve the curriculum and familial contexts which are class and ethnically located. Two conclusions that I have reached have particular significance for possibilities for change: limited opportunities are afforded by the secondary school curriculum for the boys to develop critical self-reflective skills; those boys whose sense of self is in conflict with a hegemonic masculinity experience little support for their different ways of being in the world. I argue that, through addressing these two issues in curriculum reform, possibilities for change can be created.