Ogai wielded a powerful pen in a variety of fields, including novels, translation, dramas and reviews, and fraternized with many literary figures and artists. One of them was Rohan Koda who carried out joint reviews in "San-nin Jogo" in "Mesamashi-gusa." Rohan wrote "Goju no To," a novel about the five-storied pagoda that once stood in Yanaka Tennoji, and also lived in Yanaka, which was close to Ogai's residence, for about two years from 1891. Although it is not known why Ogai started to keep company with Rohan, it is said that, since Ogai, Rohan, Koyo Ozaki and Shoyo Tsubouchi participated in a literary group organized by Soho Tokutomi who started "Kokumin no Tomo" in which "Omokage," a collection of translated poems, was printed, they began to come together. It seems that, initially, Ogai, Rohan and Tsurudo Kako, a doctor and the best friend of Ogai, were drinking companions. A letter addressed to Ogai from Rohan, in which how to eat salted fish was explained, has been preserved.

 Although "San-nin Jogo" attracted public attention for its severe literary criticisms and was feared by young writers, Ichiyo Higuchi was highly praised in it. Ogai wrote criticisms regardless of sex at that time when it was rare for a woman writer to be active. First, Ogai highly acclaimed Ichiyo in his critical essay "Shigi no Hanegaki," which was contained in the first issue of "Mesamashi-gusa," saying, "She has a rare ability to observe things." Then, Ogai expressed great admiration for Ichiyo, saying, "I am willing to give the title of true poet to her." when complete "Takekurabe" was published on "Bungei Club," a literary magazine, after "Takekurabe" appeared in "Bungakukai," a literary magazine, and got a good reputation.
 Since Ogai wanted to let Ichiyo join "San-nin Jogo" and rename it "Yotsute-ami," he sent Tokujiro, his younger brother, on an errand to persuade Ichiyo on several occasions. However, unfortunately, Ichiyo died young due to tuberculosis. Ogai also had a doctor see Ichiyo when Ichiyo was struck down by illness.

 Ogai went to the front during the Sino-Japanese War in 1894, and met Shiki Masaoka who followed the army as a journalist in the following year while Ogai was busy working as an army doctor. They talked about haiku poems in the front, and formed friendship since then. When "Mesamashi-gusa" was launched, Shiki contributed haiku poems composed by his pupils to the magazine. Also, Ogai participated in a haiku meeting held in 1896 at Shikian. It was the time when two great literary figures, Ogai and Soseki, met each other for the first time.
 Ogai was also close to Fusetsu Nakamura, a Western-style painter and calligrapher. It is said that Ogai became acquainted with Fusetsu through Shiki. Ogai asked Fusetsu to create illustrations and calligraphy several times. Especially, Ogai loved Fusetsu's calligraphy, and requested Fusetsu to write calligraphy in order to display it at Ogai's villa and Ogaisou.