High rates of gender-based violence exist in South Africa. Most gender-based violence interventions focus on providing victim empowerment services. As such, little work has been accomplished in providing preventative services, specifically those that target and prevent adolescent boys from becoming future perpetrators of gender-based violence and thus from perpetuating the cycle of violence in South African communities. The research presented in this study asks what are pre-sexually active South African adolescent boys' perceptions of gender, sex, and violence, how do various role players in their environments communicate these issues to them, and how do these boys choose to negotiate their own gender identities and gender roles? A random sample of the population of eighth grade boys at Lowveld High School in Nelspruit was drawn for this study, and from this sample, fifteen boys participated in in-depth qualitative interviews in 2004. The results of this research show that most key role players in these boys' environments, especially adult males, are not constructively communicating and engaging issues of gender, sex, and violence with them. The limited dialogue described in this study may perpetuate cycles of gender-based violence and revenge that many participants reflected on in their communities. Conclusions drawn from this research therefore call for the need for all youth-related institutions and adults- especially males- to intervene and provide coordinated and sustained positive guidance, role-modeling, and assistance as well as correct information for boys as they come of age in South African society.