This chapter examines transactional sex as a distinctive feature of traditional “dating” in Malawi. It begins with a review of the existing literature on transactional sex in sub-Saharan Africa, with particular emphasis on the distinction between commercial sex work, informal sex work, and transactional sex. It then analyzes transactional sex among a sample of 13- to 22-year-old, initially never-married females in southern Malawi. It also considers the role that cash-transfer programs in particular and social safety-net programs in general might play in mitigating transactional sex. The findings suggest that cash-transfer programs that focus on adolescent girls can allow them to steer away from “relationships of need” toward “relationships of want,” reduce risky sexual behavior as a result, and thus reduce their subsequent risk of HIV infection.