It was during the sixteenth and seventeenth centuries that the concept of human dignity began to pivot more firmly towards the notion of egalitarian moral worth that it now represents. This essay focuses on the relationship between the generations as an important place to look for markers of societal attitudes about the meaning of dignity or its absence. A valuable site of discovery is the early modern letter of advice, passed between parents and children or, in some cases, across three generations. The category of intergenerational relationship analysis is increasingly an important focus of study within the health humanities, a category of particular use in improving social cohesion and wellbeing and, therefore, community flourishing.