While love is something deeply personal, people’s intimate experiences of love are simultaneously shaped by large-scale cultural and historical processes. Anthropologists have shown how such far-reaching changes as modernization and globalization may introduce people into new ideas of affectionate relationships and transform more long-standing, social and cultural understandings of love. Often such changes bring along novel desires that disrupt traditional marital practices or create new tensions centered on contesting understandings of love. Drawing on long-term ethnographic research in Havana, this chapter explores ordinary people’s understandings and experiences of love in the midst of Cuba’s contemporary political and economic changes. Since the 1990s, Cuba has transformed from a socialist country into a new society marked by economic liberalizations, international mass tourism, and heightened inequalities of wealth. The findings show that these structural changes have created intensified complexities and contestations in individuals’ love relationships in ways that are emblematic of the emergence of sharpened social inequalities in contemporary Cuba. These results can be applied to understand the consequences that large-scale changes may have for individuals’ experiences of love in contexts undergoing drastic structural developments. The chapter concludes by arguing that the troubles that Cubans experience in their relationships differ significantly from the socialist definitions of love publicly promoted by state authorities but they are still not characterized by commodified conceptualizations. On a more general level, this chapter recommends careful ethnographic research as a fertile way for understanding cultural and historical variations in love.