The process of aging is gradually changing in urban India. In most of the gerontological literature of India, older adults have been projected as frail, disengaged and detached. However, the experience of growing old is transforming in urban areas of India. Recently a new class of older Indians are emerging who are financially independent, retain their freedom of choice, rely on means outside the family system to remain engaged and aim to have a meaningful old age. Within India, a large number of older adults who belong to the upper class, reside in Kolkata due to migration patterns, employment opportunities and urbanization. Hence Kolkata, is home to two sets of upper class older adults: those who live alone and those who live with their adult children and their families. Adopting a socio gerontological lens and relying on indepth qualitative interviews, the current study examines the lived experiences of growing old among upper class older adults of urban Kolkata. The study also draws from the social aging frameworks of activity and role theory and compares the processes of aging among the above mentioned two groups of older adults. Findings from the study suggest, that after the loss of a particular role due to life changing events such as widowhood, retirement or becoming a grandparent, older adults in both the groups develop new roles to have a purpose in their later lives. Finally, the study also highlights how gender and living arrangement determine the lived experience of aging.