The chapter provides a multi-dimensional understanding of the idea of “Grandparenthood” from the lens of psychological, cultural, social, familial and individual perspectives. The said perspectives have been drawn from research literature, observations, interviews, and experiences. Attempt has been made to focus primarily on “grandparenthood” in the Indian context; however, reference to the global context has been made where relevant. The chapter efforts to discuss the changes that have happened over time, with regard to how the role of a grandparent is perceived by the concerned stakeholders and society at large. Potential personality and socio-cultural factors that support or affect the interrelationships in the context of grandparenthood have been put in perspective. The chapter assumes a consistent theme of an intervention-centric approach to bolster inter-generational communication channels, understanding the role of changing family dynamics on grandparenthood, psyche of a grandparent and grandchild, in a view to upholding the significance of the role of grandparenthood highlighting the relevance and inevitability of the same as a source of passing on cultural values and legacy. Future implications in this area have been elaborated on, in the context of need for extensive research and more profound gerontological practice, as being the thrust areas needing focus on.