The significance of family structure on the well-being of family members is a major concept to be discussed in contemporary society. There is an impact on the overall well-being of the families due to the lack of major relationships. Hence, the major consequences that lead to the sole responsibility of children to mothers differ among locality, culture, language, etc. This study explores the psychological well-being of single mothers in relation to their role in the family, the major concepts that impact the psychological well-being, the impact of parenting, and the modes in which the single mothers cope up with the challenges they encounter. This is a qualitative (exploratory) study conducted with nine participants chosen from a convenient method of sampling located in the Kandy District of the Central Province, Sri Lanka. The sample of the research includes three each of widowed, divorced, and separated mothers. The data is thematically analyzed based on the challenges, the economic well-being, and relationship with the family and the society, the ideologies about the current status, society’s stereotypes, autonomy, the satisfaction to the present life, and their future expectations. The results of the study demonstrated that the responsibility of children, the financial crisis, confronting the society, and lack of emotional dependence to be the major challenges of single motherhood. It further stated that most of them had a strong relationship with their children and the family in comparison to the society, they found themselves to be often treated by stereotypes, and that they preferred autonomy in women. The findings of the study demonstrate that the Government should help them with self-employment, assist in the studies of their children, and conduct certain awareness programs to enhance their lives.