Gender mainstreaming in different areas of activities and policy has become one of the core themes of many nations in the Western World. While policies of gender equality have been steered in the EU member states, Eastern Europe is behind in promoting women in different roles in the society. Thus there is a need in assessing the regions specific causes of this gap. This has the potential of unveiling the full of spectrum of challenges for women entrepreneurship development as a whole and the needed shift in attitudes, aspirations and abilities to improve processes for women to be able to realise their ambitions socially, economically and politically. The publication identifies different opportunities for evidence- based backing actions at various levels of business development taken the specifics of existent attitudes in the communities they live in and differentiating rural and urban areas with their particular cultures. As a means to creating solutions, the research highlights the potential of women entrepreneurship support groups in the region that can drive gender-equality by changing social paradigms, altering attitudes through advocacy, endorsement, transfer of experience, mentoring, peer exchange and real empowerment. The publication is part of a project on ’’Promoting Women Entrepreneurship in Eastern Europe’’, financed by the European Parliament, organised by the European Liberal Forum (ELF) with the support of the Southeast Europe Office of the Friedrich Naumann Foundation for Freedom. As part of this project, three events were in organised in three cities from the Republic of Moldova, organised: a conference in Chisinau and two workshops in Cimislia and Ungheni. Some findings included in this publication are based on the conclusions from these three events.