This paper explores the institution of marriage and work organization as held by women. Both systems demand responses from women for which they are often not prepared. Their dreams of romanticised marriage and fantasy of togetherness often lead them to dis-illusionment and dis-enchantment. Their career aspirations without the reality appraisal of organisations and their own definition of systems lead them to frustrations. They are pulled and pushed between social and organization role demands, and their own entrenchment in stereotypes of role taking. The conflict between the desired and the aspired daughter-in-law, wife and mother roles on the one hand and desired, aspired professional and career role on the other hand creates conflicts, stress and guilt. Women get caught with the internalization of the normative prescriptive modalities of social and work systems. The role models from family, culture and history are insufficient and inadequate for meaningful responses. This paper explores those areas of role taking by women which can help redefine and redesign new responses in both the systems. It deals with the reinterpretation of existing roles and arriving at an integrated perspective for women which can bring convergence within both the systems of family and work. This paper suggests that women who encounter in themselves the women-person dilemma and take charge of their own destiny in their hands to give it a shape, form and a meaning finally come to make choices for the wellbeing of both themselves and the system. In the absence of such an integration, women when confronted with the turmoil of the two systems either become conformists or rebels or exile themselves and end up making compromises rather than choices.