Due to the Ukrainian crisis, relations between the EU and Russia hit rock bottom, the lowest point from the end of the Cold War. Indeed, it is crystal clear that today’s dispute is nothing but the latest chapter of a long story of misunderstandings and conflicting strategies on the post -Soviet states of Eastern Europe and South Caucasus. The further deepening of this cleavage would inflict serious damage on all interested parties: the EU, Russia and several post-Soviet states. Why is Ukraine so important both for EU and Russia? What are the real origins of the current crisis that brought to an open confrontation between Russia and the EU? What is the rationale behind Russia’s firm opposition to a further NATO enlargement? What are the viable options to escape the fate of a new ‘Cold War’?