5 Short Stories by Anton Chekhov for the Aficionados of Romance Novels

Considered by many to be one of the greatest playwrights and authors of short-stories, here are five works by Anton Chekhov exploring love and romance.

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As a physician by profession, yet writer by heart, the man responsible for producing several highly-acclaimed plays such as The Seagull and Three Sisters would reveal in one of his letters that while medicine was his lawful wife, his mistress was ultimately literature. Born on January 29th, 1860, Anton Chekhov would go on to pen hundreds of short stories in an effort to sustain his family. Known for his affairs and amorous liaisons with women, Chekhov’s literature tended to reflect his own life story as he incorporated his personal experiences with romance into his writings.

As we commemorate Chekhov’s 163rd birthday, we would like to offer readers these five short stories about the pursuit of love and fulfillment. These stories serve to inspire charm and astonishment from those who fancy the genre of romance novels.

The Lady With The Dog

The Lady with the Dog- book cover

First published in 1899, this short story introduces us to Dmitri Gurov, a man in his 40s working as a Moscow banker, leading an unfulfilling life within an unhappy marriage. Believing life to be meaningless and harboring negative sentiments toward women, Dmitri is often unfaithful to his wife and is constantly seeking new endeavors to pursue.

While vacationing in Yalta, he meets a lone woman by the name of Anna Sergeyevna walking along the coastline with her Pomeranian. Dmitri discovers that, much like his own predicament, she too is trapped in an unhappy marriage. As they commence their affair, the two come to realize that they may never meet again following their separate paths. However, the feeling of falling in love continues to haunt Dmitri long after his affair with Anna. Distraught with emotion and a deep desire to see her again, he labors to find the woman once more, unaware of the journey that lies ahead.

The Darling

The Darling and Other Stories- book cover

The theme of dependency on one’s spouse can be observed in the darling of this story, Olenka Plemyannikova. Anton Chekhov’s depiction of Olenka is thought to have been a representation of his mother with her strong attachment and devotion to Chekhov’s father. Described as a beautiful and soft-hearted young woman, Olenka falls in love with Kukin, a theater owner, and leads a happy life with her husband managing his business until his untimely demise, reducing her to a mournful widow.

However, she would develop an attachment to a new man by the name of Vasily and abandons her theater duties in favor of giving all her attention and efforts toward the work of her second husband. Olenka’s dependency on her spouse for meaning and validation is vividly depicted in this tragic, yet romantic display of affection and willingness to give, earning her the loving nickname of The Darling.

The Grasshopper

The Grasshopper- book cover

In this tale of infatuation and rejection, Chekhov tells the story of Olga Ivanovna Dymova, the wife of a modest and kind-hearted doctor, Osip Dymov. Unlike her husband who prefers to stay out of the limelight, Olga revels in the company of extraordinary guests and accomplished artists. In the presence of one such meeting is a handsome young painter by the name of Ryabovsky, with whom Olga begins an affair upon a steamboat trip. Seemingly unconcerned by her husband’s knowledge of her unfaithfulness, Olga’s adulterous relationship comes to a head with the revelation that Osip Dymov is dying of an illness, changing the trajectory of both of their lives.

A Misfortune

A Misfortune- book cover

Continuing the theme of forbidden love, Anton Chekhov’s A Misfortune explores the predicament of Sofya Petrovna, the 25-year-old wife of a notary by the name of Andrey. An old friend of Sofya’s reveals his love for her, but she rejects his advances to preserve her marriage and love for her husband. Unfortunately, as the enthralled friend remains unmoved by Sofya’s resistance, the sanctity of her marriage comes under threat.


Ionitch- book cover

Our last recommendation for all of our romance novel enthusiasts is the story of Ionitch. Doctor Dmitry Ionovich Startsev has recently arrived to a provincial town in search of work. He begins to regularly frequent the house of the Turkins, an esteemed family within the vicinity. While a guest, he takes notice of their young daughter with whom he becomes love-struck. She initially rejects his proposal and wishes to pursue her ambitions. Dmitry’s life continues as normal until the day they meet again. Can the young woman regain his forgotten passionate interest once more?

For more romantic reading experiences, be sure to check out our recommendations here! Alternatively, if you’re craving more short stories, Bookstr has you covered!