Since gaining independence, Ukraine has been stuck between the Western and Eastern integration initiatives. This has been visible from both the multifaceted judgment employed in the foreign policy decision-making and the similar domestic multi-vector behaviour that influenced the image of Ukraine as being “split” in-between. On top of that, the conflict in Eastern Ukraine, which sparked the most serious crisis between Russia and the West since the end of the Cold War, has considerably affected the sensitive positioning of Ukraine in the “inbetweener” environment. The present paper inquires how Ukraine’s image of “in-between-ness” has been transposed and evolved into a stereotyped image and whether this image is based upon valid explanations.