This paper examines the cultural framework and material evidence for teeth and oral health in later medieval Europe, using as a case study the bioarchaeological analysis of an excavated cemetery in central Italy (Villamagna). It proffers an alternative approach to the study of human skeletal material by reframing the questions that bioarchaeologists normally ask about mouths. Instead of: how much disease? what state of health? we ask: how did the mouth relate to individuals’ experiences of their world, and how might our scientific information about health and disease provide insight into wider aspects of life, society and economy? We point to a range of cultural understandings around the mouth which were changing in the central and later Middle Ages (c. 1000-1400), namely: the Bible and changing explanations for the relationships between mouth, heart, confession and experience of the divine; an evolving understanding of medicine and medical principles; and new forms of saintly intervention involved in healthcare. We then illustrate through the detailed osteobiographies of two adults from Villamagna the ways in which their oral condition reflected use-patterns and lifeways common to their communities, and shaped their individual experiences.