In this article I analyse the role of historical circumstances and individual-level aspects in the transnational relationships of Czech pre-1989 political émigrés and post-1989 migrants in Sweden and their homeland-based relatives. Using a qualitative analysis of ten life history ethnographic interviews, I look at the momentum of transnational relationship initiation, discussing the role of the political and technological obstacles and developments on the one hand, and of the voluntariness/ forcedness of the migration act and the “license to leave” on the other hand. I conclude that the structural factors which project themselves into relationship initiation strongly influence the nature of the transnational relationship throughout its course, although in different ways for the pre-1989 and for the post-1989 migrants, respectively. The article is based on the outcomes of a Master’s dissertation research conducted in 2012 as part of the International Migration and Ethnic Relations programme at Malmö University, Sweden.