This chapter examines the various instances of sympathetic engagement and emotional correspondence in Shakespeare’s Richard II. It explores the various figured audiences and emotionally engaged onlookers that the play depicts, and the ways in which the play’s characters frequently compare their sorrows to other texts and stories. This emphasis upon emotional comparability and intertextuality is intriguingly related to the ways in which Richard II is itself embedded in a larger process of literary imitation, allusion and borrowing. In particular, the chapter considers the ways in which Shakespeare borrows certain situations – and emotion words – from Samuel Daniel’s Civil Wars (1595). It is argued that play not only manipulates the audience’s sympathies but also plays an important role in refining and modifying terms such as sympathy and sympathise. In doing so, Shakespeare highlights the ways in which pity and compassion are complex imaginative processes, rather than simply automatic or humoral phenomena. At the same time, however, Richard II reminds us that such processes can be exploited in the hands of a skilful rhetorician, politician, or indeed playwright.