As Sir Philip Sidney points out in the Defense of Poesie, literature is supposed to delight and instruct. At the same time, though, Sidney also implies that every piece of literature is inherently flawed, because human writers cannot create text without errors, and human readers cannot process that text without erring in their own right. To confront this problem, Sidney invokes the concept of goodwill, asking his readers to judge textual mistakes with kindness, mercy, and indulgence, as far as they can. This attitude of goodwill, grounded in both a philosophical and a theological tradition, ultimately depends on the relationship between the author and the reader--which, optimally, is affectionate enough to encourage the downplaying of mistakes and the emphasizing of virtue-driven instruction. While this goodwill-infused method of textual judgment can backfire, causing readers to downplay or gloss over serious errors, Sidney's Defense of Poesie and Old Arcadia both imply that relationally dependent goodwill is the strongest possible methodology for maximizing textual didacticism, because it compensates as much as possible for the inherent flaws of a piece of writing. ********** NEAR the beginning of his Old Arcadia and Defense of Poesie, Sir Philip Sidney invokes the concept of goodwill. Linked to forbearance, civility, cheerful indulgence, and positive intentions, goodwill is a forgiving attitude toward errors--but, crucially, it also provides a partial solution to a tricky literary problem. From Sidney's perspective, the Fall has created a difficult situation for readers and writers, because the will present in all human beings inevitably taints literary production. In light of this fact, no human author (including Geoffrey Chaucer or Sir Thomas More) could ever create a perfect project. (1) How, then, could readers learn lessons about moral virtue, if their reading material is inherently flawed? In this article, I argue that Sidney implicitly uses goodwill as a bridging mechanism, asking the reader to gloss over the flaws of a text in order to derive maximum didactic benefit from it. The success of this project depends on the relationship that develops between the author and the reader. If a reader chooses to exercise goodwill, for Sidney, he or she becomes a member of an exclusive relational pairing (or, in some cases, a community) that deliberately opts to read with mercy, in a way that both spots flaws and downplays them in the service of a larger didactic mission. In other words, as the foundational virtue for a literary relationship, goodwill both relies on and helps to forge an intimate, near-familial bond between the author and the new reader. This bond, in turn, allows the reader to draw maximal instruction from a flawed text--partially alleviating, though never quite undoing, the consequences of the author's infected will. GOODWILL AS A RELATIONAL VIRTUE On May 23, 1584, Philip Sidney wrote a letter to his acquaintance William Temple. Still near the beginning of their relationship, Sidney had not yet seen Temple frequently enough to recognize him in public, but he is optimistic about the friendship's future progress: I greatly desire to know you better, I mean by sight, for else your writings make you as well known as my knowledge can reach unto; and this assure yourself, Mr. Temple, that while I live you shall have me ready to make known by my best power that I bear you goodwill, and greatly esteem those things I conceive in you. (2) Here, Sidney is making two moves that have ramifications for his literary works. First, he is claiming intimacy with an acquaintance through the exchange of writings. Temple's letter and book, received by Sidney, have exposed Temple's self to his correspondent in a fruitful and complete way. Second, Sidney is explaining near the beginning of the relationship that he is prepared to offer Temple goodwill without even seeing him: he admires the positive aspects of Temple's character, in a way that seems linked to the knowledge he gained from reading Temple's writing. …