Early Christian teachers and preachers were often cautious about, if not suspicious of, pleasure, but they also had a lively awareness of the psychological aspects of pedagogy, and of the power of pleasure and delight to persuade, move, instruct and even convert. This article explores the treatment of pleasure as a pedagogical tool, tracing this subject through the lens of sermons, letters, treatises and poetry written in Latin and Greek and drawing out both classical and biblical themes. It notes that, while most of the authors considered acknowledge pleasure as a potential problem in pedagogy, it is a problem they attempt to navigate. The article sketches out various approaches to the problem, noting especially the pleasure involved in reading, performing and expounding Scripture; pleasure used as a conscious educational strategy; and discussions which weigh up the dangers and gains of pleasure in education.