The story opens with our main character Olenka sitting on the steps of her father's house "doing nothing," as rain clouds gather in the distance. By way of these opening notes of boredom and a looming storm, we know that Olenka's story will not be a fortunate one.
She watches a boarder in her father's house, Kikun, complain about the coming weather. Kikun owns and operates the Tivoli, an open-air theater in town, and he gripes about how the rain is ruining his business. Well, that's only half of it, as he launches into a diatribe about the ungrateful public that can't appreciate the artistry he offers at his theater. He talks about hanging himself, about drowning the theater, about how he'd prefer hard labor in Siberia.
Olenka can't help but feel something for Kikun as he goes on and on complaining. She feels his pain, and cries for him. As the narrator explains, Olenka was always loving somebody, such as her sick father who grew increasingly ill and homebound. Given her gentle face and naive manner, she attracted the attention of men and earns the affection of women on the street, who grab her hand and exclaim, "You darling!"
Olenka's father passes away and she inherits the house. Without her father around to care for, Olenka fixates on Kikun, waiting up late at night for him to return from the theater, listening to the band playing and the fireworks going off at the Tivoli. Before long, Kikum proposes to Olenka, and they marry. It rains on their wedding day, and this only contributes to Kikun's despair.
Shortly after the marriage, Olenka begins to parrot her husband's gripes about the public and their uncultured tastes. She takes a bigger stake in the goings-on of the theater, doing administrative work in the office and intervening during rehearsals to give the actors directions. When feeling pity for the actors, she gives them money, and sometimes cries alone when she learns she's been deceived by them.
During the winter, Kikun rents the Tivoli out to other theater companies. Even though the theater makes a comfortable profit during the winter, Kikun continues to complain about the theater's fortunes. The only warmth he can muster is towards his wife who he calls his "sweet pet."
Around Lent, Kikun goes to Moscow to bring a new theater troupe to town. Olenka suffers sleepless nights, likening herself to the hens who go stir-crazy when the rooster isn't in the hen house. She hears from Kikun that he has been detained in Moscow and will be returning home around Easter, but he never does. Olenka receives a terribly misspelled telegram stating that her husband had died suddenly in Moscow, and that funeral arrangements will be announced.
She goes to Moscow for her husband's funeral, and returns home quickly, throwing herself in her bed and sinking deep into sorrow. She calls out in pity for herself, left alone by her husband's sudden death.
Chekhov encapsulates the entire drama of his story in the first three sentences. Olenka is introduced in relation to a man—her father—and shown sitting absently, thinking about nothing but the fact that it's getting dark out. Rain clouds gather, and we know things will not go well for Olenka. These three simple details are the beginnings of the threads that will be woven to make this story, as Olenka is perpetually subordinate to some man in her life and chronically devoid of any particular thoughts.
Chekhov is known as an economical and precise storyteller, famously writing, "If in the first act you have hung a pistol on the wall, then in the following one it should be fired. Otherwise don't put it there." In this instance, we don't have a pistol, but instead Olenka's near-total lack of individual personhood. This character flaw will be as crucial to our main character's undoing as a gun could possibly be. The fact that Chekhov doesn't much describe Olenka until well after he's painted a vivid picture of Kikun furthers the impression that there's not all that much you can say about Olenka, aside from the fact that she's sweet and loving.
In the first part of this story, we also get a sense of Chekhov's pitch-black humor. Kikun is so disgusted with the public's reception of his theater that he contemplates hanging himself. The solution that Kikun is jumping to is wildly disproportionate to the problem he's stating, and we get a good sense that Olenka is investing herself in someone deeply unhinged. It's even more bizarre — and again, this is the black comedy aspect of the story — that Olenka sympathizes with this man so much that she cries for him and, before long, falls in love with him.
There's a kind of arbitrary fatalism evident in "The Darling" that sows the seeds for the early-twentieth-century avant-garde literature of Kafka and the existentialists. Kikun is detained in Moscow and we don't know why. He dies suddenly, and we never know how. A telegram arrives, terribly misspelled, but Chekhov never gives us any hint of what that detail could possibly mean. We get a sense, living in this story's world, that love and life are by equal measures arbitrary.