For Chekhov contacts with Romanticism, including polemical ones, are significant in many respects. Chekhov’s intertextual connections with one of the late romantics, N. Hawthorne, are revealed. Hawthorne offers in his work his own version of the “transformation” of classical Romanticism, close to Sentimentalism (due to the promotion of the sensitivity of the characters). Chekhov is less connected with sentimentalism than Hawthorne, he switches his interest to the revival of the dichotomy of true and false Romanticism. Indeed, Chekhov consistently distinguishes between false romanticization (idealization, “idyllization”) and really justified, well-founded romanticization. This is close to Pushkin’s delimitation of “true Romanticism”, as well as the fundamental antinomy of “false” and “true” Romanticism proposed by G. Flaubert.