This article argues that Cuban ideas about gender, sexuality, and the family shaped Cuban internationalist collaboration with Nicaragua in the 1970s and 1980s. It demonstrates that collaboration sprang from a gendered political discourse, and in turn the dynamics of gendered relationships between Cubans and Nicaraguans affected the internationalist campaigns. First, the essay argues that state discourse expanded the idea of the New Man to include volunteering abroad, and cast female participants as moral agents of internationalism. Second, it analyzes the idea of revolutionary love and how it related to internationalism. Then, the article demonstrates how internationalism created transnational relationships. Finally, it examines the experiences of Nicaraguan students who went to boarding schools on the Isla de la Juventud. Throughout, the article centers the notion of family and shows how internationalist mobility created space for personal experiences, love within revolution, and new family dynamics.