The questions presented by Dostoevsky, the problems raised, the depth and level of analysis of human aspirations, the talented “dissection of the human soul” ‒ all this made his name, literally, one of the “markers” of Russian culture. The article suggests that every new reader (and, first of all, a reflexive reader) “reads” into F.M. Dostoevsky's elements of their own perception of the world and culture. Depending on the time and context, such a view can be completely different, which each time re-actualizes the texts of F.M. Dostoevsky. The article's author focuses her attention on the reasoning of the philosopher of the culture of the Russian diaspora V.V. Weidle. It is emphasized that being himself an extremely peculiar figure in domestic and world culture, V.V. Weidle accumulated philosophy, literature, history, art history, and religious studies in his works. Trying to answer exciting questions, he presented “eternal” issues in a new format, updating them in the spirit of his time ‒ speaking on the radio, sharing interviews, gathering viewers, listeners and interlocutors in a single digital space. As the principal methodology, the article's author turns to cultural-historical epistemology, which allows us to note the characteristic perspective of Weidle's view of Dostoevsky: his understanding of Dostoevsky, as well as interpretation as a “prophesying” author in the context of V.V. Weidle.