This article examines the acquisition of pragmatic competence in L2, applying this stimulating area of research to premodern texts in a way that has yet to be done (to the author’s knowledge). Specifically, this article discusses the teaching of “challenging” incongruent speech behaviours (such as sarcasm, banter, and irony) in a group of Anglo-Norman dialogues of the late Middle Ages. The present work focuses on the representation of incongruent speech acts in the dialogues, how this representation speaks to a pedagogical method that incorporated humour, and also the possible functions of humour in the pedagogical environment. The topic of incongruent performance and its pedagogical implications will also be considered. By discussing the depiction and role of incongruent speech behaviours in the dialogues, I argue that these texts were sophisticated teaching aides that may have used humour as a pedagogical tool to teach more difficult elements of language use.