HIV prevention poses, individual and contextual, challenges to South African youth. The study is a pilot project that aims to develop theory, employing methods of critical social research; and the theoretical perspectives of social constructionism and communities of practice. The nature of Gergen''s concept of reflexivity is investigated, amongst a group of South African adolescents who live in an informal settlement in the Eastern Cape. The conceptualization of reflexivity, in this study, includes discourses that simultaneously: challenge mediators of HIV prevention, describe multiple positions of knowledge, include critical reflection; and indicate a choice on the best way forward after considering the implications of making a particular decision. The nature of the participants'' reflexivity and the reflexivity of their characters, was explored, and described using the Reading Guide method. The reflexivity of the participants emerged in the process of describing characters, within stories and a role play, which argued for or against engaging in sex. The study found that participants employed different discourses according to a characters'' gender.