This article explores the subjective experience of nationality and (trans)national belonging based on biographical interviews with two groups of Jewish participants born in Bulgaria before the Second World War, and residing in Bulgaria and in Israel, respectively. I focus on their retrospective accounts of the mass exodus to Israel in 1948–1949 and the maintenance of transnational family and kinship ties thereafter, during the Cold War. The comparison brings into relief the challenges of their integration into the respective national contexts, and the ways in which the memory cultures in the two countries have molded biographical reminiscences. I argue that despite these differences, a unique case of a transnational generation is at hand, formed by their past experiences as well as by the re-negotiation of these experiences, which was made possible from the 1990s on.