This paper analytically points out the challenges that India will have to face in the process of reaping anticipated demographic dividend rather than intriguing a pessimistic or optimistic perspective. Both empirically and theoretically there is nothing automatic about the link from demographic change to economic growth. Bulging of population in the working ages merely generates the potential for economic growth and hence window of opportunity created by the population bulge may remain underexploited. Based on a conceptual framework this paper tries to understand the critical mechanism of reaping demographic dividend and examines this process for India. Evidences show that the widow of opportunity period for India is probably lasting in between the years 2015 and 2040, though it is not exactly satisfying UNDP definition of windows of opportunity. A two percent increase in working population will be accompanied by 13 percent increase in old age population from 2005-2050. The ratio of number of jobs to working age population has increased from 1:17 to 1:25. Disease adjusted life expectancy is only 53.5 years and poor nutritional status makes early physical setback. Low adult literacy and decreasing public sectors employment poses socio-economic security problems. These will altogether lead to an early initiation of aging in the life course. A comparative assessment with other countries shows that projected economic status of India is well below other developed and developing countries. India will have to negotiate on these issues circumspectly to catch up with the economic standard set by countries such as USA and China; otherwise, India will get old before getting rich.