© 2019 Journal of International Women's Studies. The aim of this paper is to analyze the convergence between the current state of education, labor markets'' preparedness, and expectations of Generation Y females taking Bahrain as a case study. Generation Y is defined as the group of people aged 30 years and under. Although Generation Y is a worldwide phenomenon and members of this generational group share certain characteristics globally, in Gulf Cooperation Council countries [GCC] they display strong pressure to succeed, a need of gaining a high salary but also to acquire knowledge and expertise; and a preference for a strong work-life balance. In addition, in the workplace they seek peer orientation of the superiors rather than sheer respect for hierarchy; the latter is especially visible among the female population. The quickly modernized and globalized world created a generation with worldviews distinctive from the generation of their parents and this is especially visible in the GCC region that has been undergoing profound changes in the last decades with more and more women entering the labor market. GCC countries are at a stage where the transformation of their labor markets remains of utmost importance; hence this paper will shed light on the current trends and provide recommendations for future reforms.