This interview of Gregory Randall offers a lens onto a transnational life experience, including that of international refugees in Cuba. Randall was born in New York in 1960. He spent his early childhood in Mexico and arrived in Cuba in 1970, where he remained until the 1980s. In this interview, Randall reflects on Cuban policies toward women, homosexuality, and youth. He also analyzes his own family’s experience, characterized by a strong commitment to reflecting the Cuban Revolution in its own social relations and its ways of living and loving. The interview provides a unique perspective on these challenges and on Cuban history, shaped by Randall’s particular position in that historical process. Unmoored from national frameworks, his subjectivity is anchored in a transnational Left sensibility. He belongs to a generation of children of the revolution, part of Socialist Cuba as children and teenagers, and belonging to Left and internationalist families.