The successful aging model marked by an emphasis on the self has dominated the gerontological tradition in a majority of the western industrialized countries. However, this narrative of active, socially engaged and consumer centric aging is not a contextually homogenized process as experienced by older adults elsewhere, where a “meaningful decline” defines older adults’ renegotiation with familial relationships, expectations, religion and death. Borrowing social-psychological and gerontological perspectives the current study examined the co-existence of these two contrary models-disengagement and successful aging- in two cities that are in transition Ahmedabad (Gujarat, India) and Saskatoon (Saskatchewan, Canada). Drawing from in-depth interviews this study examined intergenerational relationships and expectations around filial ties, emotional bonds, network ties, cultural ideologies and their contribution in forging the aging identity in these two contexts among older Indians in Ahmedabad and those in the transnational setting. Findings suggest that despite the Asian traditional values and expectations surrounding caregiving and support from adult children older Indians in Saskatoon have reconfigured their expectations and are re-negotiating between the two cultural worlds by embracing the successful aging model. In contrast, a structured dependency in terms of economic support and psychological needs is preserved, legitimized and nurtured in the older adult-adult children relationship in Ahmedabad where older parents contribute to household and grandparenting duties while expecting caregiving, support and respect in exchange. By adopting a comparative perspective, the study demonstrates how everyday life of older adults is constructed, lived and produced and role of cultural forces shaping the experience of growing old.