The literature produced during the Middle English period in England is varied and diverse. It is held together, in part, by language, though dialect and regional differences do contribute to the diversity. However, the audience of these works, whether they are secular romances or devotional treatises, would have been similar; in fact, there would have been much overlap. This essay addresses two Middle English works—Chevelere Assigne, a chivalric romance, and Ancrene Wisse, an anchoritic treatise—arguing that there is a great deal more shared by the two works (and genres) than just language. Positing that both works might have been read by the same audience—anchorites pre- and post-enclosure—I will argue that anchoritic texts echo the metaphors and themes of chivalric romance, particularly those associated with maternity, language, and gender. Drawing on the works themselves, shared imagery, and shared representations of motherhood, desire, and the natural world, I will offer an explanation of the shared aspects of these genres as part of the diverse and complex culture of the early Middle Ages.