This thesis is an ethnographic study of the lives of thirty community HIV educators in KwaZulu-Natal, South Africa. Compared to quantitative studies this is a small number, but by keeping the number of participants small it has been possible to obtain an extensive understanding of the lives of each individual, which helps to explain why they make the decisions they do. The reason for choosing community HIV educators as the participants in this study is because it could be stated from the outset that they are well-informed about HIV prevention and, depending on the specific NGO they work for, they have been recipients of either ‘female empowerment’ or ‘responsible masculinity’ programmes. This is significant because early HIV prevention interventions have assumed that providing individuals with HIV awareness and gender equality programmes would lead to the implementation of HIV preventative behaviour. Studying the willingness and ability to implement HIV prevention practices of these particular individuals could therefore help to answer the question whether HIV awareness and gender-related programmes are indeed sufficient to create HIV preventative behaviour change. Furthermore, it was useful to hear from these participants what they experience as enabling and restricting factors when it comes to implementing HIV preventative behaviour. The core research question is: How do community HIV educators in KwaZulu-Natal negotiate HIV prevention in their everyday intimate relationships? The data presented in this thesis was collected during ten months of participant observation amongst community HIV educators whilst they were at work, at home, or out with their peers. To further aid the general understanding of Zulu culture, the researcher lived as part of a Zulu family for six months. The thesis presents several examples of community HIV educators who do not consistently use condoms in their everyday lives despite the fact that they promote the use of condoms. How is it possible that those who speak of being transformed as a result of HIV awareness and female empowerment or responsible masculinity programmes, and who promote condom use in their communities, do not always consistently use condoms in their personal lives? This thesis is concerned with trying to resolve this apparent illogicality. It argues that when individual interventions fail to lead to behaviour change it is because individuals act in relation to other people instead of in isolation. The thesis draws on the work of Bourdieu, particularly his concepts of habitus, field, and capital, to explain how structural factors influence individual practice. This means that the negotiation of HIV prevention is affected by what is generally considered appropriate in terms of existing dispositions. Hence the perception of a particular HIV prevention practice as either appropriate or inappropriate affects the ability of an individual to implement this practice. Examples are provided of how, when it comes to the practice of condom use, which has generally been perceived as inappropriate, structural factors have a restricting effect on HIV prevention. This thesis also provides examples of how, when it comes to the practice of medical male circumcision and virginity testing, which have generally been perceived as appropriate, structural factors actually have an encouraging effect on HIV prevention. As a result this thesis argues that instead of addressing individuals, HIV prevention interventions should address the collective. However, this thesis also argues that an increase in economic, cultural, social, and symbolic capital can suppress the effect of structural factors. To support this argument the thesis attends to individuals who, when they can afford to do so as a result of having capital at their disposal, deviate from collectively determined ideal practice, for example by discreetly negotiating HIV counselling and testing with their sexual partners.