This article focuses on Malawian sex workers' understandings of exchange and intimacy, showing how multiple historically emergent categories and specific work pragmatics produce specific patterns of relational meanings. As we show, sex workers make sense of their relationships with clients through two categories. The first is sex work; the second is the chibwenzi, an intimate premarital relational category that emerged from pre-colonial transformations in courtship practices. These categories, in turn, are also shaped differently in different work settings. We use narratives from in-depth interviews with 45 sex workers and bar managers in southern Malawi to describe how the everyday pragmatics of two forms of sex work-performed by "bargirls" and "freelancers"-foster distinct understandings of relationships between them and men they have sex with. Bargirls, who work and live in bars, blurred the boundaries between "regulars" and chibwenzi; freelancers, who are not tethered to a specific work environment, often subverted the meanings of the chibwenzi, presenting these relationships as both intimate and emotionally distant. Through this comparison, we thus refine an approach to the study of the intimacy-exchange nexus, and use it to capture the complexities of gender relations in post-colonial Malawi.