This paper addresses the European Union’s attempts is to construct a new model of regional cooperation that includes not only economic objectives but also social, cultural and environmental agendas with this Eastern Neighborhood. This ambitious aim is however facing challenges stemming from its inherent mix of traditional realism and idealist notions, as well as the political and cultural contestations increasingly laden with tension. Building on the lessons learned from the recent crises with their multiple effects, this paper questions the EU’s ability to balance security prerogatives with improved regional cooperation and conflict resolutions and discusses the EU policies affecting the Eastern Neighbourhood in terms of re-territorialisation that merges traditional geopolitical concerns and politics of regional difference with a post-national focus on mutual interdependence and partnership. Despite its welcoming rhetoric, the EU can be seen to act with respect to its neighbours as a border-confirming and border consolidating agent, inscribing ‘otherness’ between itself and its neighbourhood, which highlight the tension between attempts to consolidate the union and to enhance the EU presence beyond its borders. The concurrent EU attempts will then be projected against Russia’s actions affecting the region, Ukraine in particular, that now more concretely than ever finds itself in the sphere of influence of competing global actors and in the midst of great power geopolitics. The implications of these competing interests to the wider Europe and its security will then be addressed.