Empathy is a broad concept that involves the various ways in which we come to know and make connections with one another. As medical practice becomes progressively orientated towards a model of engaged partnership, empathy is increasingly important in healthcare. This is often conceived more specifically through the concept of therapeutic empathy, which has two aspects: interpersonal understanding and caring action. The question of how we make connections with one another was also central to the work of the novelist E.M. Forster. In this article we analyse Forster’s interpretation of connection—particularly in the novel Howards End—in order to explore and advance current debates on therapeutic empathy. We argue that Forster conceived of connection as a socially embedded act, reminding us that we need to consider how social structures, cultural norms and institutional constraints serve to affect interpersonal connections. From this, we develop a dispositional account of therapeutic empathy in which connection is conceived as neither an instinctive occurrence nor a process of representational inference, but a dynamic process of embodied, embedded and actively engaged enquiry. Our account also suggests that therapeutic empathy is not merely an untrainable reflex but something that can be cultivated. We thus promote two key ideas. First, that empathy should be considered as much a social as an individual phenomenon, and second that empathy training can and should be given to clinicians.