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Drawing upon critical health and discursive psychology, the study explores the sexual decision-making of 8 sexually-active high school girls, aged 17 to 19 years, living in Masiphumelele, a poor African community in Cape Town, South African. The girls participated in a focus group and 1-2 individual, semi-structured interview/s. The paper describes and explores, firstly, the ideals girls uphold surrounding sexual relationships, on the one hand, and the normative character of sexual relationships as these typically play out in practice, stressing the dissonance between the two. The paper highlights the part that boys and girls play in reproducing a problematic sexual culture that supports sexual relationships that are antithetical to girls' ideals, and the processes that mediate sexual conformity. Following this, the paper turns to explore the participants' sexual decision-making and relationships. Three broad sexual strategies are isolated. The paper explores the rationale driving the respective strategies, the extent to which these strategies produce relationships that conform to, or, alternatively, diverge from and counter the norm, and the factors and processes mediating this. Finally, the paper explores and highlights the role of relationships beyond the sexual arena in mediating girls' sexual decision-making, and how these are implicated in reproducing problematic sexual norms and relationships. The study finds that the barriers to girls establishing and sustaining sexual relationships that promote emotional and physical health and well-being are deeply embedded within aspects of the psychosocial and material environment. Promoting the emotional and physical health and well-being of girls within their sexual relationships requires recognising and addressing problematic elements within their broader relational environments, and providing supportive, advisory figures and contexts, as well as positive role models.