Without autobiographical confessions, letters or diaries, critics can only make attempt to make connections between known events when speculating on the influence of an author's life upon their work. There are some facts known about Chekhov that accord at least in part or in general ways with the story "The Lady with the Pet Dog." Chekhov was in Yalta to undertake a cure for his tuberculosis when he wrote this story. He, like Gurov, was very bored with his stay there. Unlike Gurov, however, he was distressed because he was away from the woman he loved. Also like Gurov, Chekhov found true love late in life with Olga Knipper whom he eventually married, even while under the fatal cloud of tuberculosis.

Undoubtedly, while at Yalta, Chekhov heard those stories Gurov's narrator mentions:

immorality in such places as Yalta are to a great extent untrue; he ... knew that such stories were for the most part made up by persons who would themselves have been glad to sin if they had been able .... ("The Lady with the Pet Dog")

Thus such immorality as Gurov's would have been called to Chekhov's attention. Another similarity is that Chekhov is known to have had the same sort of sympathetic bond with women that Gurov has while both character and author nonetheless remained aloof and disconnected from deep human intimacy--until each found true love.

there was something attractive and elusive which allured women and disposed them in his favour; he knew that, and some force seemed to draw him, too, to them. ("The Lady with the Pet Dog")

Some critics speculate that it was Chekov's experience at Sakhalin Island--a penitentary colony where he had a deeply meaningful realization about the human condition--that provided the model for Gurov's psychological change at the end of the story. Other critics suggest that his true love with Olga was sufficient for the characterization of Gurov and his changing psychological motivations.