The reality of aging is felt in places like Kerala in India and Biberach in Germany. Active Aging as defined and propagated by the World Health Organization has been found to be a holistic and encompassing way to represent the multidimensional world of elderly and aging. Capacity of design to visualize scenarios and create options thus transforming given situations into more preferred ones has been used to varying levels of success in Transformation Design projects. Yet, there are only a few examples of papers with a design-led enquiry into the complex and compelling area of aging studies. Play has a quality to be a self-motivating, intrinsically driven, communicative process with the capability of being accommodative and allowing for co-creation and uninhibited expressiveness. In this research project, the author provided 26 participants with a playful environment using color-coded Lego blocks and a demarcated base plate. They came from middle-income backgrounds, existing in two distinctive cultural contexts of Biberach in Germany and Kerala in India. By employing the Lego blocks, they could construct their own representation of aging. This was done on two distinct time lines and around nine broad aspects. The resulting semi-structured interviews followed by data analysis using Grounded Theory method brought out the role of Engagement as a meaning-making as well as a coping strategy in the life and living of elderly participants. This design study clearly indicates the possibility of employing Play as a mediator in dealing with complex system dynamics to create opportunities for further intervention.