This article considers Dave Eggers’ 2013 dystopian novel The Circle, which critically explores digital surveillance, alongside Georg Simmel’s social-theoretical writings on the secret, social distance and proximity, and the intersection of social circles. The article shows how Simmel’s social theory illuminates important aspects of secrecy and surveillance in The Circle, including the secret’s constitutive role in individuality and social relations, and allows one to reframe the estranging effect of certain dystopias in terms of Simmelian strangerhood, which is based on the paradoxical unity of closeness and remoteness in social-spatial relations. Conversely, The Circle in certain respects pushes beyond Simmel’s social theory by using literary devices to critically explore social subjectivity and by highlighting elements of 21st century life that challenge or complicate Simmel’s sociological claims. Especially notable in this respect are The Circle’s insights into the affective intimacies between people and their personal technologies that shape our digital social practices. By bringing Simmel’s social theory and The Circle into productive dialogue, this article lays the groundwork for an approach to analysing dystopia that more fully appreciates the genre’s sociological import – including how at least some dystopias implicitly engage in social theorising – than prevailing, literary-formalist approaches to the study of speculative fiction.