The radical ideas that arose from the Enlightenment movement had major influences on Westernized societies, including that of the United States. This period marked a major shift in philosophical, political and scientific thought from that of traditional ideology to an emphasis on reason and actions that maximized happiness for the majority. This paper will be an examination of modern American culture, positive psychology and their connections to these principles. The objective is to approach this exploration from the perspective of the feminine experience, including a discussion of gender roles and their implications on well-being. It will then be proposed that the cultivation of authenticity through the support of positive psychology focus areas—character strengths and virtues, meaning and purpose, emotions and mindset—can empower women on both the individual and collective levels. From there, women can be conduits of authenticity in their relationships and external environments, forging a path toward feminine and collective flourishing, as well as positive change in our current climate.