An almost forty-year-old man from Moscow named Dmitri Gurov has been staying in Yalta. About two weeks into his stay, he hears people talking about a young woman who is frequently seen walking along the seafront with her small Pomeranian dog. Dmitri has taken an interest in the “fresh arrivals” at Yalta but he is particularly keen to catch a glimpse of this woman and her dog. He notices her for the first time while he is seated at Vernet’s outdoor café because she and her dog walk past him on the promenade. Dmitri then runs into her repeatedly in the municipal park and in the square, although the two of them never interact. He notes that the woman is “fair” but short and that she is always alone (except for her dog) and always wearing the same cap. Nobody in Yalta appears to know her name and they simply refer to her as “the lady with the dog.” Dmitri is intrigued by her friendless state and feels that he should introduce himself since she is never in the company of friends or a husband. 

The narrator then explains that Dmitri has a family: a wife, a twelve-year-old daughter, and two sons. Dmitri is unhappy, however, because he dislikes his shrewish and intelligent wife that he had been talked into marrying during his second year of college. He is disgusted with his wife’s aging features and finds her imposing. The narrator notes that Dmitri is in “awe” of his wife despite simultaneously finding her “shallow, narrow minded, and dowdy.” Dmitri “dislike[s] being at home” and, as a result, has had numerous love affairs. Although Dmitri disparages women and calls them “the lower race,” he secretly acknowledges that he is more at ease in their company than in men's. Dmitri may be a serial adulterer but he is never fully satisfied by his affairs. He feels that every affair begins pleasantly but ultimately spirals into an “excessive complication” which produces an “intolerably irksome situation.”

One day, “the lady with the dog” sits down next to Dmitri to eat in the public gardens. The man pets her dog in order to strike up a conversation, asking the mysterious woman if he can give her dog a bone. The woman agrees and the pair begins to talk. He learns that she is called Anna Sergeyevna, that she is married, and that she has come to Yalta on vacation. The older man is intrigued by the exuberant naïveté of this young woman and acknowledges that it was not so long ago that she was a schoolgirl like his daughter. He notes that this is probably the first time in her life that she “found herself alone, and in a situation in which men could follow her and watch her, and speak to her, all the time with a secret aim she could not fail to divine.” At the same time, Dmitri also recognizes a trace of sadness in her character and finds her “pathetic.”