In the context of the academic interest shown in the enduring transnationalism of contemporary migrants and in the modes of transitions to adulthood in different global settings, in this article we examine the transnational lives of adolescents moving between Vancouver (Canada) and Hong Kong. While there is a lot of literature on the parents' political and economic calculations, there is very little on how adolescents in these situations articulate their geographical sensibilities. We draw on three periods of fieldwork undertaken in 2002, 2008 and 2010 during which we employed a transnational methodology to interview young people in Vancouver and Hong Kong. We argue that becoming an adult involves a process in which, in their discussions about the geographical and emotional distance between themselves and their families, young people articulate their own complex emotions towards specific places in their transnational social field. Their families sporadically interrupt the adolescents' otherwise independent lives with fragmented modes of supervision. By examining the complex intentions and emotions behind circular migration from the perspective of transnational youth in a community of split families, we advance the discussion on transnational geographies, particularly of the family in the context of a flexible global economy.