Wilhelm Dilthey’s historical and systematic research has been a crucial yet controversial source in the history of the social sciences and social philosophy. This contribution reconstructs Dilthey’s critique of historical reason and the controversies surrounding it. Dilthey’s early shift from theology and metaphysics towards historical interpretation and structural-functional social explanation has been seen as a precursor to subsequent developments in philosophy, history, and the social sciences. However, critics described his emphasis on the structural formation of the individual and relational individualism, the pre-reflective self-reflexivity, autobiographically situated self-reflection of lived experience in first- and second-person perspective, and the elementary role of interpretive understanding in practical life and the human sciences as remnants of idealism, romanticism, and liberalism. After outlining Dilthey’s philosophical development and his models of relational individualism, self-reflexivity, and the interpretive stance, this chapter examines the “primacy of the social” assumed by Dilthey’s critics and consider to what extent Dilthey’s strategies might still address practical existence and its systematic study in the social sciences.