This volume brings together related examples of medieval didactic dialogues. Texts of this kind were designed both to instruct their readers or audience in doctrine, wisdom, morality, and Christian truth, and at the same time to entertain them through witty verbal exchanges, enigmas, and riddles. The texts that have been assembled here grew out of a common source that originated in Latin writing. However, no Latin text that can be identified as a witness to the source has survived, and to help compensate for this missing part of the textual tradition, the editors have reconstructed a Latin version using clues provided by the vernacular texts. Those edited here are: the Old English Prose 'Solomon and Saturn', the Middle English 'Master of Oxford's Catechism', the Old English 'Adrian and Ritheus', and the Old Icelandic 'Dialogue between a Pupil and his Master'.