Oppression
Everywhere you turn in the short stories of Chekhov you will find folks either crumbling under the heavy weight of oppression or in active revolt against it. Sometimes the oppression is systemic like the expectations of adhering to societal conventions rebelled against by the lady with the pet dog and her adulterous lover, but very often the oppression is individualized like that suffered by Olinka in “The Darling.” Of course, all individual oppression is merely a reflection of systemic oppression so in reality the weight threatening to crush Olinka is exactly the same as that which Anna and Gurov hope to overcome. When writing in Russia during the Tsarist rule, it was probably impossible for any writer not to address the nature of oppression, but the stories of Chekhov show an especially keen sensitivity without lapsing into didactic symbolism at the expense of very real characters.
Fatalism
Does oppression create the fatalism or is systemic fatalism a necessary tool for successful oppression? Try to get at the answer to that question as you story after story by Chekhov where direct agency on matters of destiny is never within grasp of his characters. Circumstances arise that are simply beyond the control of most; certainly those peasants and members of the working class in Russian under the Tsars. If a person does not accept that what will happen will happen, then he will likely become one of Chekhov’s more unfortunate victims.
Loneliness
There is never enough empty space on the stage for Chekhov to examine the heart-wrenching effects of loneliness. Wise enough to recognize the limitations of different forms of written expression and talented enough to exploit the strengths of those different forms, Chekhov’s great lonely Russians populate his short stories almost exclusively. The previously mentioned Olinka is one great example, of course, but not for nothing is the story of Iona Potapov’s loneliness titled “Misery.” Arguably the most iconic and certainly one of the most well-known figures who personify this theme is the lawyer who makes the titular wager in one of Chekhov’s most anthologized stories, “The Bet.” For a chance at wealth, he willingly sacrifices fifteen years of freedom only to wind up not just lonely and broken, but the victim of one of literature’s greatest welshers. While loneliness is certainly a recurring theme, it must be noted that his characters never achieve the tragic dimension of Dostoevsky's great lonely men, but that is only because they are usually fatalistic at the outset whereas Dostoevsky's characters actually believe--or at least strive to believe--in a benevolent god.
Communications Breakdown
Reading a Chekhov short story can be a frustrating experience sometimes. The unhappiness and loneliness and alienation sometimes seem like could be avoided if only the characters could learn how to properly communicate with each other. Even a relatively humorous and more lighthearted story like “A Work of Art” reveals the problems that stem from communication when a poor patient unable to afford to pay a doctor for his services results in an ill-advised attempt at bartering involving a work of art that the doctor accepts with the full knowledge that the content make it impossible for him to ever exhibit it in public. The lack of communication here is more abstract than usual, but becomes the impetus for an unlikely series of events that produce the humor of the story. Generally, however, the inability of characters either to adequately express themselves or not even bother trying has far more tragic results.
