One important critique of the “West’s” hegemony in international relations (IR) theory has been this theory’s inability to come to terms with the problem of difference or the Self/Other dialectic. To further highlight the importance of the Self/Other relations, this article proposes to analyze Russian theoretical discourse of relating to Europe and the West. For centuries, Russia has participated in intense interactions among European, Asian and Middle Eastern regions, and it has developed a language and theories for relating to its various Others. Studying Russian debates can assist us in the task of reflecting on problematic epistemological and ethical assumptions behind IR scholarship, as well as suggest some paths to a genuinely diverse and global IR theory. To research both continuity and progression of Russian arguments, I draw cases from imperial and post-Soviet historical periods and analyze their debates—Eurocentrism and Eurasia—in terms of assumptions their participants held about interacting with the Other. Although moving beyond viewing the East/West interaction as something mutually exclusive has been a challenge to Russian thinkers, some of them have found ways to conceptualize the two cultural entities as in dialogue with one another and to learn from opposing perspectives.