This article explores the reasons why dialogue has been such a key part of religious education by examining several texts from the medieval period: Gregory the Great's Dialogues, Petrus Alfonsi's Dialogue against the Jews and three hagiographical narratives from tenth-century Spanish manuscripts. It will argue that when read or listened to, the dialogue of the text was meant in turn to cue an internal dialogue, a response within the self, and a transformation. While meditative religious reading of all kinds was thought of as producing this inner reflection and debate, the dialogue format was an especially effective didactic tool for inculcating in beginners a mode of internal reflection and questioning, inspired by an outside source. Finally, although the content and even the message of the dialogue that is written or overheard may be fixed and clear, its effect on those who read or hear it remains open and provisional. It is up to readers or listeners to draw their own conclusions and absorb their own lessons from it.