This chapter explores how the concept of sympathy is explored and interrogated in three Elizabethan prose texts: John Lyly’s Euphues: The Anatomy of Wit (1578); Sidney’s The Old Arcadia (c. 1580); and Thomas Lodge’s Rosalynde (1590). Lyly’s Euphues represents an important transitional moment in the history of the concept, as it employs both the earlier Latin form sympathia and the newer English word sympathy to describe the ‘sympathy of manners’ between two male friends: Euphues and Philautus. It is argued that the pair share each other’s emotions because of a common set of circumstances, rather than sympathetic magic or humanist models of friendship. The chapter reads these three prose fictions in the context of other works that reproduce or complicate the notion of a ‘sympathy of affections’ between friends or lovers. Within this discourse we can see the term sympathy increasingly used to describe a correspondence of woe, or what the narrator of Anthony Munday’s translation of Palmerin (1588), in a suggestive modification of the trope, refers to as a ‘sympathy of afflictions’.