The article is about the history of hermeneutics in the USSR, more precisely ‒ about one of the significant episodes of this history ‒ the school of philological hermeneutics V.G. Admoni and N.O. Guchinskaya, which arose and developed at the Leningrad State Pedagogical Institute, at the Department of Germanic Philology in the second half of the 20th century. It is shown that the scientific activity of this school, in fact, represents the evolution of the philological problems of the theory of translation into the philosophical problems of understanding as a key method of humanitarian knowledge. The translation became a model of the hermeneutical situation, which was described not in terms of the concept of linguistic structure and communicative act, but in terms of expression of unique creative (poetic) meanings created by the artist and recreated by his recipient. The understandable hermeneutic situation was presented in the concept of N.O. Guchinskaya as a starting point for the study of any cultural artifact that precedes its idealization and schematizing generalizations. Hermeneutics in this concept has become a kind of transition from art to science ‒ both as a research method, based on the intuition of the researcher, and as a result of such work, which turns out to be the recipient’s response to the author’s creative incentive. The article also shows that this transition is a circle that is the only way to access the world of culture, historically distant from the world of the researcher. We are talking about a circular alternation of grammatical and psychological interpretations that set the boundaries of interpretation but allow you to save all their diversity and infinity.