Olenka mourns Pustovalov much like she mourned Kukin, weeping profusely and declaring that she should be pitied for being left wretched and miserable. But unlike after Kukin died, Olenka spends much longer mourning in isolation. It's six months before she even leaves to go to market, and her fellow townsfolk can only venture to guess what her life is like.
They do spy Olenka in her house—frequently she is talking with the veterinary surgeon, who reads her the news. Olenka tells a woman at the post office how badly the town needs a veterinarian for its domestic farm animals, saying their health is as important as human beings' health. During this conversation, Olenka repeats exactly the same things the veterinarian says, and it becomes obvious that she has fallen for this man. She does a poor job keeping this a secret, telling men from Smirnin's regiment all about cattle plagues and similar concerns. Smirnin gets annoyed by this and chastises Olenka, but she sobs and asks why they can't just be happy. The embrace and all is well.
Well, that is, until Smirnin leaves. He is sent away with his regiment, and Olenka finds herself desperately alone once again. This launches a period of despondency for Olenka, when nothing rouses any emotion or brings her joy. She has to force herself to eat and her house falls into disrepair. It's during this time that she comes to realize that she has no ideas or opinions at all. She looks around and finds nothing that can rouse any opinion from her, and she realizes how different this is from when the veterinarian was around. Naturally, this thought troubles her.
But one day, Smirnin shows up at her door. He has left the military and has reunited with his family. They are put up in a hotel while he looks for lodging. Olenka excitedly offers that his family can lodge in her house, and when he accepts, Olenka starts to fix the place up. When Smirnin arrives with his family, Olenka is taken with his son Sasha, a chubby 10-year-old boy.
She begins obsessing over the child, and when he tells her that an island is a piece of land surrounded by water, she repeats that back to him. The narrator tells us that this is the first opinion that Olenka has held in years. At dinner with Smirnin and his wife, Olenka begins parroting everything the boy says about his school, offering all of the young boy's opinions and indignities as her own.
Eventually, Smirnin's wife leaves once again to live with her sister and never returns. Smirnin becomes busy with his job and is never around. Olenka finds herself feeling sorry for the boy, and invites him to stay in her part of the house. She begins acting like a mother to him, waking him up for school every day and encouraging him to stay on track with his schooling. She walks the boy to school and finds herself full of joy as she watches him go up to the building. Sasha has roused a great maternal feeling in Olenka, and it gives meaning to her life, making her look years younger.
She fixates on the young boy as they spend all their time at home together. Olenka helps him with his studies and prays over him when he sleeps. But one day she hears a knocking at the door and jumps to the conclusion that it's a telegram from the boy's mother, demanding that he leave to go stay with her. But it is just Smirnin returning home from a late night on the town. Olenka goes back to sleep relieved.
The story ends with Olenka falling back asleep, hearing Sasha cry from the other room, "I'll give it you! Get away! Shut up!"
James Joyce once said of Chekhov's plays "There is no beginning, no middle, and no end, nor does he work up to a climax; his plays are a continuous action in which life flows on to the stage and flows off again, and in which nothing is resolved... His drama is not so much a drama of individuals as it is the drama of life." And indeed, while Joyce is not talking about Chekhov's literary fiction, Joyce's analysis applies to "The Darling" just as well.
For example, there is no discernable climax in The Darling, but instead a series of tragedies and moments of renewed hope, when Olenka finds a new man in which to invest her energy. As for a beginning, middle, and end, the story instead takes on a cyclic structure, where when one relationship ends tragically, another soon begins. We see this occur in condensed form after Pustoltov's death, with Olenka going through this cycle twice: once with Smirnin and then again with Smirnin's son Sasha. The cycle is only broken for a brief period of time after Pustolatov's death, which gives us a window to peer in and see the true nature of Olenka's dependency on men.
And indeed, Joyce's remark that Chekhov's stories utilize the drama of life seems especially poignant in this case. Of course there is the constant play of life and death—itself a key dramatic component of narratives across the ages—but it is also a play about the nature of family life. We watch Olenka get abandoned by way of strange twists of fate over and over again, yet the final abandonment that we know will eventually hit her is Sasha simply growing older and eventually leaving home. With the talk of him going on to become a doctor or an engineer, this is simply the way things are supposed to be. In turn, Chekov wrings the drama of life from a strange approximation of the mother-son dynamic, and lends a trajectory to Olenka's strange life that we know will stretch past the temporal confines of this short story.
The implication, like Joyce says, is that Chekhov's stories are left unresolved and his characters have lives that flow both inside and outside the scope of these stories. Sasha's lines at the end of the story are confounding if we seek in them some meaning that will help us decipher the peculiar story we just read—and perhaps they do hold some cryptic meaning that will help us decode "The Darling"—but they can also be simply understood as utterings during a bad dream that will become part of his and Olenka's continuing story. Chekhov chooses not to resolve "The Darling" with this ending, but to give us a hint of how these lives might continue. After all, the only real resolution in life is death, yet for Olenka, a death never resolved anything.