Ukraine belongs among those young countries where the beginnings of democratisation and nation-building approximately coincided. While the development of nation states in Central Europe was usually preceded by the development of nations, the biggest dilemma in the Ukraine is whether a nation-state programme — parallel to the aim of state-building — is able to bring unfinished nation-building to completion. Ukraine sways between the EU and Russia with enormous amplitude. The alternating orientation between the West and the East can be ascribed to superpower ambitions reaching beyond Ukraine. Eventually, internal and external determinants are intertwined and mutually interact with one another. The aim of the paper is to explain the dilemmas arising from identity problems behind the Ukraine’s internal and external orientation.