This article takes as its stimulus Adriana Cavarero's recent investigation of the postures of rectitude and inclination in the Western philosophical tradition (Cavarero 2013). To showcase how this book might catalyze productive interactions between feminist critics in different areas of the humanities, I will bring Cavarero into dialogue with a thinker she mentions in passing who extensively develops “rectitude as a general principle” (Veyne 2003): Seneca. I argue that a gendered ontology of rectitude is increasingly put under pressure and transformed in Seneca's Epistles, and propose that the letters are a laboratory for developing a new model of inclination that arises from an urgent need to confront the consequences of political impotence and threats to bodily integrity for Roman aristocratic manhood in the 60s ce. The playful, densely literary Epistles offer multiple points of contact with Cavarero's own philosophical strategies, and emerge as a highly stimulating text for feminist thinkers interested in the ethical and political implications of acknowledging vulnerability. Reading Seneca alongside Cavarero reminds us that such investigations have a (tortuous, buried) history in Roman antiquity whose recovery is itself politically significant.