Medieval scholars and theologians wrote more commentaries on the Song of Songs than any other biblical text. From a modern perspective, this focus on the Song of Songs seems odd—why did these men devote so much attention to what appears to be a rather explicit love poem? Why would a love poem even be included in the Bible at all? Many medieval intellectuals answered these questions by arguing that the Song of Songs was not a rapturous exchange between two human lovers, but an instructive dialogue between Christ and the Church in which Christ implores the Church to spread his message through preaching. This talk will examine several instances of this type of interpretation and the effects they had on the development of evangelization within the medieval Church.