What is being sad and how do we define it? Recent studies argue that sadness is not just one emotion but psychological and physiological responses vary according to the relevant triggering situation. Linguistic usage shows that the ancients had developed the very same awareness. This paper explores a set of metonymy-based emotion words related to distinctive behavioural patterns and expressing sadness in ancient Greek and medieval Christian culture. It traces ethical changes in the perception of negative emotions subsequent to loss of agency and powerlessness based on a wide array of sources going from the Homeric poems to the Church fathers. While bringing evidence of cross-linguistic and cross-cultural constants in the way we build the basic constructs of our life, this talk will show how the very notion of sadness was deeply challenged by the Christian revolution. In so doing it will also prove that the way we talk does not simply reflect on the way we feel but also determines our worldview, constantly re-shaping our emotional regimes.