This volume brings together examinations of pragmatic meaning and proverbs of the Medieval North. Pragmatic meaning, which relies upon cultural and interpersonal context to go beyond the simple semantic and grammatical meaning of an utterance, has a fundamental connection with proverbs, which also communicate a deeper meaning than what is actually said. Essays in this volume explore this connection by examining the language of generosity, conversion, friendship, debate, dragon proverbs, and saints’ lives. These essays are inspired by the works of Thomas A. Shippey, who has been a pioneer in the study of wisdom poetry and pragmatics in medieval literature.