The purpose of this article is to explore Simmel’s radical psychosociology of modernity. To this end, we address the intersubjective constitution of individuals in Simmel and deal with the concept of the psychological expansion of roles, qualities and individuality. We then address the tension between the modern social and the modern individual, mask and shame, and the question of sociability and “alienated sociability.” The analysis and the integral interpretation of the psycho-sociological foundations of Simmel’s work allow us to conclude the article by stressing the potentialities of this approach to analyze the relationships between intersubjectivity and emancipation.