By the late 1990s, when I was conducting ethnographic fieldwork research in Lisbon, the ‘dentists’ case’ had become a familiar trope for the presence of Brazilian immigrants in Portugal. Although it involved a small group of Brazilian and Portuguese professionals, it gained visibility in the media of both countries, escalating into a political and diplomatic quarrel, and culminating in the amendment of the 1966 Cultural Accord. I use Victor Turner’s concept of social drama to address the case as a chapter in the cyclical pattern of connection and disconnection of postcolonial Luso-Brazilian relationships. Drawing from a recent discussion on the concept of cosmopolitanism in migration studies, I employ the idea of postcolonial sociabilities to help explore the seemingly inherent ambiguities in the relationship between Brazilians and Portuguese.