The aim of this thesis is to catch glimpses from the everyday life of grandparents living in the Roman Empire between 200 BC and 400 AD. A topic that has hitherto been under-examined, despite the increasing amount of scholarship acknowledging (recent) changes within the culture of grandparenthood. Indeed, socio-anthropological studies mentioning grandparents in previous societies remain, most often, limited to stereotypes, a shortcoming this thesis addresses. Drawing on Latin epigraphic evidence, literary texts and legal sources, we ask what can be ascribed to cultural patterns and expectations towards grandparents as well as individual realities and attitudes. The thesis subjects evidence regarding the position of the grandparent within the Roman family to a quantitative as well as qualitative analysis, supported by a catalogue of hundreds of epigraphic examples on the one hand and carefully selected case-studies on the other. We show that family composition and parental authority (or the lack thereof) are defining characteristics in the relationship between grandparent and grandchild. Furthermore, the sources attest to a remarkable flexibility and inclusivity in Roman familial mentality. As such, this study aspires to contribute to present-day debates concerning inclusion and elderly care strategies. To this end, four elements of discontinuity between grandparenthood then and now are established, i.e., (1) the disappearance of the two quintessentially Roman concepts patria potestas and pietas, (2) a decrease in mortality rate, (3) the Industrial Revolution enabling an increased mobility, and (4) an increase in state intervention in family life, e.g., state-funded pensions. Despite these elements of change, the thesis argues that a remarkable continuity is to be recognised within the image of (and expectations toward) grandparents. That is, the image of the grandparent as the old and frail, yet wise guardian of tradition and culture. With contemporary grandparent culture shifting from 'old' to 'hip', this thesis is an essential resource for understanding and redefining a new generation of grandparents.