To A. N. Pleshcheyev, 3 August 1889. Yalta.

August 1889 falls in the darkest stretch of Chekhov’s year: his older brother Nikolai, a talented but dissolute painter, had died of tuberculosis at the family’s Sumy estate on 17 June, and Chekhov – who had nursed him through the final weeks – fled south afterward, first toward the idea of a trip abroad, then, as this letter recounts, only as far as Odessa and then Yalta. The letter is addressed to Alexei Nikolayevich Pleshcheyev (1825-1893), the poet, former Petrashevist exile, and literary elder statesman who by this period served as Chekhov’s warm, avuncular link to the "Severny vestnik" ("Northern Herald") circle – hence the errand in Section 4 asking Pleshcheyev to reassure "Anna Mikhailovna" (Anna Mikhailovna Evreinova, the journal’s editor) that a promised story would arrive by 1 September. That story is almost certainly "Skuchnaya istoriya" ("A Boring Story" / "A Dreary Story"), which Chekhov was drafting through the summer of 1889 and which did appear in Severny vestnik that autumn; its own melancholy, "dullish" tone (Section 10) is very much a function of the mood this letter describes.

The letter performs cheerful deflection over real grief: the compulsive comic patter about ice cream, deaf typesetters, and a near-miss with a bathhouse pole sits directly beside the admission that he left "a dreary tedium and dread" at home, and that conscience says he ought to go back. Chekhov does not name Nikolai or the death outright, but the "things not right at home" (Section 3) is that bereavement, and the letter’s determined jokiness reads as characteristic self-management rather than indifference. Nothing here needs softening, but a reader coming to this letter cold should have that context so the humor is not mistaken for callousness.