In May 1887 Ivan Bunin published his first poem “Village Paupers” (Деревенские нищие) in the Saint Petersburg literary magazine Rodina (Motherland). In 1891 his first short story “Country Sketch (Деревенский эскиз) appeared in Nikolay Mikhaylovsky-edited journal Russkoye Bogatstvo. In Spring 1889, Bunin followed his brother to Kharkov, where he became a government clerk, then an assistant editor of a local paper, librarian, and court statistician. In January 1889 he moved to Oryol to work on the local Orlovsky Vestnik newspaper, first as an editorial assistant and later as de facto editor; this enabled him to publish his short stories, poems and reviews in the paper’s literary section. There he met Varvara Pashchenko and fell passionately in love with her. In August 1892 the couple moved to Poltava and settled in the home of Yuly Bunin. The latter helped his younger brother to find a job in the local zemstvo administration. Ivan Bunin’s debut book of poetry Poems. 1887–1891 was published in 1891 in Oryol. Some of his articles, essays and short stories, published earlier in local papers, began to feature in the Saint Petersburg periodicals.

Ivan Bunin spent the first half of 1894 travelling all over Ukraine. “Those were the times when I fell in love with Malorossiya (Little Russia), its villages and steppes, was eagerly meeting its people and listening to Ukrainian songs, this country’s very soul,” he later wrote. In 1895 Bunin visited the Russian capital for the first time. There he was to meet the Narodniks Nikolay Mikhaylovsky and Sergey Krivenko, Anton Chekhov (with whom he began a correspondence and became close friends), Alexander Ertel, and the poets Konstantin Balmont and Valery Bryusov. 1899 saw the beginning of Bunin’s friendship with Maxim Gorky, to whom he dedicated his Falling Leaves (1901) collection of poetry and whom he later visited at Capri. Bunin became involved with Gorky’s Znanie (Knowledge) group. Another influence and inspiration was Leo Tolstoy whom he met in Moscow in January 1894. Admittedly infatuated with the latter’s prose, Bunin tried desperately to follow the great man’s lifestyle too, visiting sectarian settlements and doing a lot of hard work. He was even sentenced to three months in prison for illegally distributing Tolstoyan literature in the autumn of 1894, but avoided jail due to a general amnesty proclaimed on the occasion of the succession to the throne of Nicholas II. Tellingly, it was Tolstoy himself who discouraged Bunin from slipping into what he called “total peasantification.” Several years later, while still admiring Tolstoy’s prose, Bunin changed his views regarding his philosophy which he now saw as utopian.

In 1895–1896 Ivan Bunin divided his time between Moscow and Saint Petersburg. In 1897 his first short story collection To the Edge of the World and Other Stories came out, followed a year later by In the Open Air (Под открытым небом, 1898), his second book of verse. In June 1898 Bunin moved to Odessa. Here he became close to the Southern Russia Painters Comradeship, became friends with Yevgeny Bukovetski and Pyotr Nilus. In the winter of 1899–1900 he began attending the Sreda (Wednesday) literary group in Moscow, striking up a friendship with the Nikolay Teleshov, among others. Here the young writer made himself quite a reputation as an uncompromising advocate of the realistic traditions of classic Russian literature. “Bunin made everybody uncomfortable. Having got this severe and sharp eye for real art, feeling acutely the power of a word, he was full of hatred towards every kind of artistic excess. In times when (quoting Andrey Bely) “throwing pineapples to the sky” was the order of the day, Bunin’s very presence made words stick in people’s throats,” Boris Zaitsev later remembered. He met Anton Chekov in 1896, and a strong friendship ensued.