Drawing on a larger ethnographic study of four high school young men, this paper foregrounds high school male-male friendships as a context for examining how heterosexism and homophobia operate to limit and delimit the ways masculinities are constructed. I begin this article by first highlighting an inconsistency between recent school initiatives aimed at "helping boys" improve literacy scores and emerging safe school initiatives that recognize and support a diversity of gender identities in Canadian schools. I move from this point to illustrate how compulsory heterosexuality emerges when high school young men attempt to develop male-male friendships. The final section describes the fear and homophobia that restrict and confine relationships among high school young men. In the light of the complex ways masculinities are negotiated among and between young men invested in friendship practices that transgress a dominant normative masculinity, the article concludes with a call to develop and ensure safe spaces exist for all students. (Contains 1 note.)