The article demonstrates the evolution of relations between V.V. Rozanov and D.V. Filosofov, on the basis of changes in their participation in the political life of Russia. The author shows the initiating role of D.V. Filosofov, as an editor, in the appearance of a number of V.V. Rozanov’s articles on aesthetic topics. Based on D.V. Filosofov’s letters, the article proves his admiration for the literary talent of V.V. Rozanov. At the same time, the critic was distinguished by his rejection of the political views advocated by the newspaper Novoye Vremya, with which V.V. Rozanov collaborated. The author notes that after the revolution of 1905, D.V. Filosofov repeatedly tried to convince V.V. Rozanov to join the active political opposition. The example of V.V. Rozanov’s assessment of D.V. Filosofov’s political role indicates a change in his own views on political events in Russia. A.P. Filosofova, D.V. Filosofov’s mother, following the interests of her son, switched to friendly relations with V.V. Rozanov and his wife V.D. Butyagina. Being a leader of the women’s social movement, A.P. Filosofova supported the Religious and Philosophical Meetings initiated by V.V. Rozanov and her son. She managed to draw V.V. Rozanov to the side of the women’s rights movement. The thinker had previously been skeptical about that trend. The image of the mother of the former admirer of his work, given in V.V. Rozanov’s articles, became one of the reasons for the rupture of relations between the writers. As a result, the memory of her as an embodied idea of innate vitalism served as the main motive for the thinker to reconcile with D.V. Filosofov at the end of his life.