Several international organizations have advocated for worldwide adoption of sexuality education in formal education systems. Notions of sexuality in Africa, however, have often been viewed from Western perspectives and yet Africa has distinct overarching socio-religious philosophical worldviews, which determine the way its people recognize, define and assign meaning to sexuality. While some cultural beliefs converge with guidelines of Western-oriented sexuality education programmes, some constitute a different psychological frame of reference from that which informs Western-oriented school-based sexuality education models. A thorough knowledge of the cultural beliefs and practices is crucial for a better understanding of the psycho-social dimensions of sexuality education programmes in Southern Africa. This chapter discusses African philosophical worldviews and their relatedness to sexuality. The chapter also unveils indigenous forms of sexuality education and their historical evolution, highlighting common myths and taboos and their potential effects on implementation of Western-oriented sexuality education programmes. The fact that some aspects of indigenous sex education have survived for centuries despite relentless efforts to eradicate them is testimony to their tenacity and perceived usefulness. Youth are, therefore, torn between the prescribed unreserved and sometimes confrontational Western-oriented sexuality education curriculum and conservative traditional modes. Considering the duality of forces of indigenous systems and globalization in this era of HIV and AIDS, it is imperative for designers of sexuality education curricula to draw from strengths of the coexisting heritages and to build an integrated pedagogy that is culturally relevant, within the framework of global trends.