In the article on the basis of comparison of texts of the story “Pure Monday” (1944) and religious-philosophical treatise “The Liberation of Tolstoy” (1937) offered a new perspective on understanding the philosophical structure of the novel from the series “Dark alleys”. The article states the dependence of the ideological and figurative system of the story to philosophy of death (“philosophy of care”) by L. Tolstoy. The author argues that the plot of the story is a love story “he” and “she”. But at the level of reflection of the philosophical ideas (the author says) Bunin’s heroes are the abstract personification of the artist love to the thoughts and ideas of the writers-predecessors. The image of the heroine of “Pure Monday” is the idea (the personification) of Bunin’s love to the philosophical views of the late Tolstoy. The image of the main hero is embodied in his character the reflection of Pushkin’s ideas about the world, his “Onegin type”. The conflict of different life philosophies becomes a “condition” of failed love.