The article concerns ways of interpreting key concepts of V. Pelevin’s “Sleep” (such as “time”, “sleep” and “death”) in the English translation made by A. Bromfield. The ways of rendering original allusions and realia that are difficult to translate are in the focus of the study. Peculiar time movement is presented in the original in two contradictory ways: the explicit story of Nikita Dozakin covers several months of his youth, though many hints supported by certain historic allusions and social realia convince the attentive reader that the plot covers several decades and Nikita gets old and dies some time before the end of the story. Some of these realia (for example, “em-el philosophy” = “lectures on Marxism-Leninism”) have been skillfully explicated and rendered by A. Bromfield, but some interpretations lead the reader astray, as the word “spirits” instead of the Soviet soldiers’ slang “dukhi”, used for “dushmany” (Afghan militants) during the war in 1979-1989: “We’ve taught the spirits, and the spirits have taught us”. The whole scene lost its temporal location and besides mystic connotation got some connection to alcohol. Realia and allusions to Soviet and Yeltsin’s times, pointing to changing age and social status of the hero, are described in the article according to their function in the text and potential translatability. Using the data of the survey carried out among American students who had read ‘Sleep” in translation, the most sophisticated passages in the text are revealed, and the ways of their interpretation for English-speaking readers are offered.