This article examines the strategies for creation of the images of the Other and the One-of-Us as exemplified in postmodern prose and dramaturgy (Evgenii Grishkovets’ drama Zapiski russkogo puteshestvennika [Notes of a Russian traveler], 2011; Maria Arbatova’s dramatic travelogue Po doroge k sebe [Eng. trans. On the Road to Ourselves, 1998], [1992] 1999; Vladimir Tuchkov’s hypertext novel “Russkii I Tszin” [Russian I Ching], 2009; Valerii Kislov’s comical treatise “Kratkii kurs u-vei” [A short course on wu wei], 2009). The close attention to the images of the East and the West and emphasis placed on similarities and differences with the Russian worldview is driven by the transitional character of Russian culture and its search for identity. The dominant strategy emerges in reviewing the outdated images of the Other and the One-of-Us. By creating these images, the authors employ a range of strategies: demythologization/mythologization, inversion, and apophatics. The common intention of the works lies in promoting cultural dialogue.