Family and intimate relationships across borders is a central topic in migration literature. This article investigates the representation of the transnational family in Dime algo sobre Cuba (1998), by the Cuban writer and filmmaker Jesús Díaz. Written from exile in Spain, the novel is set in Cuba’s “Special Period” of post-Cold War economic crisis and emigration of balseros (‘rafters’). The highly original plot of a twofold perilous voyage between Havana and Miami incorporates elements from both exile literature and undocumented migration narratives, but it also goes beyond the established patterns of these genres. Drawing on transnational family studies and feminist theory, this paper examines how the characters experience the migration process with focus on the internal dynamics of the subjects that comprise the family, their relations to multiple places, as well as the narrative modes of representing these relations. It shows the internal dynamics of the protagonist’s family as a split narrative of dis- and reintegration across political and national borders. It also discusses the lived experience of the double orientation of the migrant subject, facing a lost home(land) as well as a new place which s/he still does not inhabit. The analysis suggests that the process of the reorientation of the migrant subject is articulated as a gendered and sexualised narrative of the intimate relations of the protagonist, intertwined with the narrative of the homeland. However, the ambivalent ending of the novel with its references to cultural hybridity points to an opening where the future of Cuban exile and diaspora lies in the ability to forgive and establish cultural contact across borders.