Concern about the health and wellbeing of young women has made teenage pregnancy and motherhood an important focus of research in South Africa. As an educator in a secondary school in South Africa, I was aware of the number of teenage mothers in school. I aimed to gain insight into how a group of teenage mothers understood sexual risk especially within a context of high HIV prevalence. In some cultural and social settings, teenage motherhood while still in school deviates from notions of “ideal” circumstances of both motherhood and schooling and continues to be surrounded by disapproval and stigma. I therefore regard this as sensitive-area research. Researching at the school at which I was employed both aided and hindered my research. I learned that conducting qualitative enquiry in sensitive areas presents many research challenges, and the relationship between myself, my study, and my supervisor was critical. I chose to use semi-structured interviews as my main data generation method because it allowed me to speak privately to the teenage mothers, to ask similar questions to all participants and also allowed me the space to probe when necessary. In this case, I discuss my research project and its context, the practical aspects of doing postgraduate research at a university, the planning and implementing of semi-structured interviews with teenage mothers in school, the need to constantly reflect on and revise research strategies, and the tensions between guidance and freedom within the supervision relationship. Postgraduate students embarking on research projects will benefit from my reflections and insights about the dynamic relationships between the research project, the methodology, and the supervision.