Objectives: This paper focuses on the bilateral relationship between the EU with Russia, discontinuing regular bilateral summits, suspending the dialogue on visa issues, and talks on a new bilateral agreement to replace the PCA. The policy of combining gradual sanctions with attempts to find diplomatic solutions to the conflict in eastern Ukraine was being followed by the EU. The efforts of the E3+3 group of countries with Russian participation that concluded a nuclear agreement with Iran in July 2015 raised hopes for greater cooperation on the global stage. Discussions: It concentrates on elements that must be considered to understand and predict their actions in between the relations of two players, the image each of them has of themselves. Understanding these elements in Russia and EU case, the EU's image of itself and of Russia and Russia's image of itself and the EU is an essential pre-condition to pre-empt possible problems in the relationship and devise effective strategies on how to solve them. Conclusion: It concludes that the systemic incompatibility will remain which will be the key problem between Russia bent on sovereignty and hard power, and the EU integration machine, and with its imperialist bureaucratic culture, which is structurally incapable of accommodating a Russia disinclined to submit itself to Western normative hegemony. Their relationship will remain stagnant and crisis-prone unless the EU's approach to Russia changes along with the Russian policy itself. The policy on both will be reactive rather than proactive and will lack cohesion and consistency.