This chapter examines Shakespeare’s interest in sympathy – both the word and the concept – and his representations of emotional correspondence between individuals, both real and imagined. Shakespeare’s works explore the relationship between the earlier understanding of sympathy as likeness and harmony (‘If sympathy of love unite our thoughts’ (2 Henry VI, 1.1.23)) and its newer association with ideas of compassion and commiseration (‘O what a sympathy of woe is this’ (Titus Andronicus, 3.1.148)). It is argued that Shakespeare was sceptical about the rhetorical ideal of sympathy as a straightforward or automatic process. After exploring a range of early Shakespearean texts the chapter focuses on Romeo and Juliet, which contains a notable example of the word sympathy, as the Nurse describes the shared emotions of the lovers: ‘O woeful sympathy! / Piteous predicament!’ (3.3.85-6). The fact that this speech contains some unintentional double entendres complicates both the Nurse’s sense of idealised harmony and the audience’s affective response. Shakespeare demonstrates that our commiseration for the sufferings of others is not simply the product of passive imitation or occult sympathies, but rather comes about through a combination of choice, thought, and judgement – and may differ significantly from the ‘original’ emotion being observed.