The modern scientific paradigm of linguistics that replaced comparative historical and linguistic-centric paradigm is focused on the relationship between language and reality which is inherently asymmetric in nature. In this situation, the problem of an accurate and complete mutual understanding of the participants of communication becomes more and more urgent. This problem considered in the framework of cultural studies suggests the division of cultures into high context cultures, i.e. those where the behavior of communication participants does not directly express their goals and intentions, and low context cultures, implying direct and frank manifestations of those intentions. The author applies the idea of high and low contextuality to the Russian language, setting the task of identifying those typical manifestations of Russian discourse in which the linguistic signs show a high dependence on the situational and verbal context, and in this way, by virtue of the language structure, cause difficulties for mutual understanding. From this point of view, the study investigates the polysemy of Russian words and grammatical forms, as well as the conditions in which their unambiguous understanding is or is not achieved. It emphasizes the insufficiency of merely stating the possibility of several solutions and the need for algorithms that provide the only (or not the only) correct solution. The author sees another obstacle for successful communication in hyperonyms that do not have a distinct hyponymic content for each participant of communication. The third obstacle is the omission of the verbal designation of modifying and / or substantial characteristics of reality. The article emphasizes that those who speak Russian, in principle possessing the resources necessary for overcoming these difficulties, seek to use them effectively only in certain specialized areas (science, sports, trade) and do not care about the maximum adequacy of language units and reality in everyday and political discourse. In conclusion, the article describes how to take into account the noted features of the Russian language when consciously learning Russian as a native language, as well as when teaching it as a foreign language.