This project investigates the art of listening in Japan through ethnographic observation of hostesses (escorts) and listening volunteers, and an analysis of self-help literature on listening. At night clubs in Tokyo, hostesses, who are famous for being good listeners, use listening as a streetwise skill. This enables them to stay in subordinate and supportive positions, and to help customers dominate a conversation. The customers can gain a sense of recognition, enhance intimate relationships with the hostesses or rebuild their masculinity. Hostesses’ listening is ‘an interactional weapon of the weak’, gaining money, business connections and prestige, but this, in turn, intensifies the gendered division of labour in interactions. By contrast, listening volunteers – who converse with elderly people using listening as a tool for reaching out – sometimes fall short in conversation, not realising that their listening functions as a gift. This forces clients to stay in helpee/subordinate positions and makes them feel obliged to reciprocate. Listening here can be ‘a mask for silent authority’. Superficially these two cases do not resemble each other; however, both deal with power dynamics. Their other common aspect is performing emotional labour. These listeners suppress or discard their feelings – such as disgust or boredom – and generate socially required emotions like respect or compassion, whilst displaying situationally expected listening behaviour. They hope to generate a certain state of mind in others to a greater or lesser extent, and so must perform emotional labour. Listening is therefore a subset of emotional labour. Self-help guides implicitly instruct emotional labour, and tacitly suggest dealing with power relations by introducing therapeutic listening for superiors and ‘zealous listening’ (my term) for subordinates. As my analyses show, listening is not simply a skill of hearing or understanding others, but also a way of associating with them. Therefore, listening is an ‘art’, which requires both fundamental skills, and a listener’s own personal way of relating to others.