In this paper, I look into personal and political entanglements in Rosa Luxemburg’s letters and essays revolving around questions and problems of the revolution. The analysis is informed by Hannah Arendt’s theorisation of revolutions in modernity, as well as her reading of narratives within the political. What is intriguing about the Luxemburg/Arendt encounter is the fact that although both theorists consciously refused to connect themselves with feminist ideas and movements of their times and geographies, their writings have inspired a rich body of feminist theorisations of the political. What I argue is that Luxemburg’s ideas and lived experiences of the revolution largely inspired Arendt’s theorisation of the revolution as a political phenomenon in the pursuit of freedom, and are opening up new vistas in our understanding of gendered dynamics in historical and contemporary revolutionary events.