The article examines the originality of I. S. Turgenev's and A. P. Chekhov's artistic dialogue based on the stories The Diary of a Superfluous Man, A Boring Story, and the novel Fathers and Sons. Among Turgenev's works, the story The Diary of a Superfluous Man stands out as a significant artistic discovery. Not only does Turgenev capture the important features of his contemporary ("the ordinary" man of the 1840s), but he also creates a typologically universal character.