The study examines the experiences of contemporary older Czech men specifically in their role as grandfathers. Despite the great body of research devoted to the issues of grandparenthood, most attention, both locally and internationally, has been given to women and grandmotherhood. To overcome this shortcoming, we present findings based on eleven qualitative interviews conducted with men with diverse grandparenting experiences and performing various forms of caring practices. Grandparenting is a negotiated, relational, and highly gendered social role, which we explored in our research through our respondents’ narratives focused on everydayness and memories of their own experience as a grandchild. Based on their self-reflective narratives we were able to describe the performative potential of grandparenting and define four types of activities through which grandfather roles take shape. On this basis we were also able to describe the spatio-temporal aspects of these practices, which proved to be crucial for understanding of gender issues of grandfatherhood. Although the narratives of the participants in our research reflect an active approach to fulfilling the grandparenting role, their caring practices are still predominantly structured in a gender-stereotyped way. In terms of theory, our research results build on and seek to contribute to one of the most influential theoretical models of grandfathers’ involvement proposed by Bates and Taylor.