The article analyzes the evolution of relations between Russia and the European Union, as well as the impact of the Ukrainian crisis on them. The purpose is to define the conceptual obstacles to mutual understanding between Moscow and Brussels. Decisions taken on the line Moscow-Brussels, during the events of the period 2014-2015 are fundamental in analyzing the bilateral dialogue and narrow spectrum of possible interactions. Are also analyzed the main problems in relations between the parties arising from the wrong perceptions, distrust and misunderstanding on issues of common interest and mutual respect. In the actions of both parties stands noticeable lack of strategic planning, from where appears also the inertia of relations between Russia and the EU. At the same time, the interdependence of bilateral cooperation, and understanding the need for stable cooperation for internal development of each of them does not enable the parties to move to the direct confrontation.