As a consequence of Cuba’s severe mid-1990s economic crisis and the government’s attempt to remedy it by investing in the tourism sector, a new interactional space has opened up, providing Cubans with the opportunity to form economically advantageous relationships with foreigners. This thesis contributes to the anthropological understanding of the lifeworlds of Cuban women who engage in relationships with foreign men that are sexualized and commercialized to various degrees. These touristic encounters are morally and ideologically contested in late socialist Cuba. They are also characterized by an ambiguous tension, as the women have to manage foreign men’s expectations regarding exchanges of love and money. Based on six months of fieldwork in Havana, I examine the components and developments of such relationships and discuss the women’s particular role. I highlight their agency as they capitalize on touristic desires and fantasies of the exotic and erotic Caribbean Other, simultaneously reproducing a system of sexualized, racialized and gendered inequalities. Through a discussion of the methodologies employed in the research, I question the analytical use of empirical categories in anthropological analysis. I argue that emic categories applied to relationships between Cuban women and foreign men are political and normative markers of social statuses, but are not valid analytical units.