The article aims to prove the adequacy of intercultural communication realized with free translations. The method of comparative linguistic analysis of the original text and its translation used in the article defines free English translations of Bulat Okudzhava’s poems taking part in the intercultural dialogue of Russian and English-speaking readers. Consequently, the carried out analysis outlines main features of free translations. The most prominent among them are: the adequacy coefficient > 20%, a system of maintained semantic connections with the original, a relatively high artistic value of the translation. As a result, the identified features mark free translations very high in the hierarchy of poetic translation typology and recognize their significant role in an adequate dialoguing of intercultural communicants. The material of this research can be applied in the theory of both literary translation and intercultural communication.