Singlehood is seen as a lifestyle capable of successfully fulfilling human needs. In today’s society, more and more people are choosing to live alone. Single living refers to a household consisting of one person. Singlehood is a multi- dimensional problem. The study is significant at two levels. First and foremost, it is proposed to bring out the factors and problems of singlehood. Secondly, to reveal the relevance of the support system and the life satisfaction level in the life of single women. Present study is an analysis of the dilemmas faced by the single women of Kerala. The Singleton has emerged as a distinct social category in the rapidly changing Kerala society. The present study attempts to show the change from Spinster to Singleton and the generation differentials of single women in Kerala. The study also made an attempt to find out the socio-cultural background of the single women, the factors that led women of Kerala to singlehood, their adjustment to this status, the stress associated with it, the problems they encounter, the support system they enjoy and the level of life satisfaction they have in their unique life style.