Marriage plays an essential role in the Indian setting. It is considered a sacred union of not just two individuals, but of two families. Regarded as a must for social approval, a marriage has tremendous psychosocial and economic impact on family members and their resources. Paradoxically, remarriage in India is still looked down upon due to cultural beliefs and the frequently associated stigma with a “failed” marriage. While there may be negative experiences from a previous marriage that might impact how receptive one is to a new relationship, social acceptability plays a major influential role as well. If there are children from the previous spouse, it raises additional concerns. The patriarchal culture and fear of child neglect often contribute to a gender bias, discouraging women from remarrying. Men find it comparatively easier to remarry. Remarriage in the elderly is further difficult as it is met with disapproval from family members, especially children and grandchildren. Ageism is a bias that prevents the society from understanding the needs for companionship in the elderly. This establishes psychosocial barriers that prevent the older generation from freely exercising their basic right to live life on their own terms, fall in love, and enjoy an active sexual life. Elderly are already a vulnerable population with high prevalence of anxiety, depression, and feelings of loneliness. Remarriage in this subset of community often creates a taboo that compounds the existing social exclusion and in turn adversely affects their mental health and functional capacity.