This article investigates how and why medieval ecclesiastical writers thought and wrote about experiences of grief in human history. It examines the works of three late twelfth-century Latin writers from England: a foundation history of Waltham Abbey and its holy cross, a series of annals kept by Hugh Candidus at Peterborough, and Gerald of Wales's autobiographical and travel writing alongside his De principis instructione. Drawing on biblical, literary, theological, and iconographic models for grief and suffering in the western Christian tradition, the article situates these works in the exegetical and philosophical ideas they shared, and explains what is original and significant about their approaches to each instance of grief. It argues that the central problem these writers pondered in their narratives was the relationship between the universal and particular nature of grief. Grieving, they thought, had three key qualities: it impelled a desire to act; it could not be meaningfully measured; and it persisted in time. In prioritizing the experience of grief over its function, meaning, or morality, these writers considered the emotion rational, natural, and honest. The value these writers placed on human family or family-like relationships provides the context for understanding their priorities in thinking about responses to loss. Interest in grief's endurance, rather than its resolution in consolation, has been understood as more typical of secular, not sacred, thought. By showing how these writers’ ideas about grief's nature lived alongside and within other ideas of Christian thought, this article illuminates a greater range of medieval ecclesiastical ideas about the dignity of human history and emotion.