The following reflection looks at contemporary relationships with a painful past, within a dual socio-anthropological perspective. On the one hand, the focus of interest is on the social conditions of reconstruction and expression of “memory”; on the other, it takes into account the ways in which traces of the past are mobilized and re-appropriated and may, from an individual perspective, even define existence. The aim is to analyse the plurality of individual and family narratives told by the retornados, using a generational perspective: one made up of individuals born in Angola in the decade 1930–40; another made up of their children, also born in Angola, and repatriated as children or adolescents; and yet another made up of individuals born in Portugal after 1975. The study focuses on seven Portuguese settler families that were rooted in Angola for longer than a single generation. These family trajectories illustrate the difficulties and limitations of analysis in terms of “white retornados” and “non-white retornados”.