This chapter offers a history of same-sex sexuality in South Africa, making connections across the colonial, apartheid and post-apartheid periods. Theorising the book’s notion of restlessness, the chapter also presents a theoretical overview of transnationalism in relation to contemporary and historical cultural flows. Post-apartheid is widely imagined as a fixed chronotope, neatly demarcated in time and space, rather than as a dynamic moment restlessly produced at the intersection of various local and transnational movements and discourses. The connectivity that is discussed in this chapter highlights the links that post-apartheid same-sex sexualities have to both historical routes and contemporary global networks of sexual politics.