In autumn 1886, after returning back to Tiflis, Toumanian started to attend city library, at the same time he dreamed about continuing his education in a higher school. Apparently, his attempts to continue his study didn’t have any result.
Contrary to his strong desire to study, Toumanian, who is in an uncertain situation, had to work in one of the stores for a very short time. During that time, he also took on the duties of a private teacher in a “bazaz-agha” (fabric merchant) family.
After leaving school, Toumanian continued to have meetings with a small group of literate young people, the main members of which were from Lori. They were Anoushavan Abovyan, Tigran Veranyan (Vren Tashretsi), Yegor Kharazyan.
In July-August 1887, Toumanian’s first writings appeared in the press, he flooded the pages of “Nor-Dar” and “Mshak” with a series of anecdotes from the life of the Lori people.
In the same period, Toumanian, contrary to his inclinations, took the position of a scribe in the Armenian Consistory of Tiflis only for taking care of his daily needs with the minimum salary he received (16 r. 66 k. per month), and for the opportunity to engage in literature and continue his studies in the future.
Although the job was mechanical and torturing for him, the position in the Consistory gave him chance to get acquainted with society representatives’ – those who visited the institution with various questions – life condition, daily worries, behavior and morals, psychology.
His visits to the villages of Lori and other regions with the consistory members-priests, in order to examine spiritual affairs, greatly contributed his life experience enrichment. The impressions and thoughts from that visits were included in the travelogue “In Borchalu” and the review “Criminals and Witnesses”.
In September 1887, during one of his official visits, Toumanian met and fell in love with miss Mariam (Olga) Machkalyan who was the adoptive daughter of the Qamoyan Church’s priest and the Consistory member Hovhannes Martirosyan.
Ter-Hovhannes approved Toumanian’s intention to marry to Miss Machkalyan, with condition that the poet should become a priest. The young man in love had to sign the proposed contract. According to that contract Ter-Hovhannes should take care of the newly created family until Toumanian would become a priest.
On March 24, 1888, Hovhannes Toumanian and Mariam Machkalyan engagement took place. On that occasion, Toumanian wrote a quatrain poem entitled "Artsvik" (not preserved).
In April of the same year, with the consent of the bride's parents, he moved to Ter-Hovhannes' apartment on Norashen Street, taking with him all his possessions: “A bed linen and two books” – the novel “Wound of Armenia” and an issue of “Hyusisapayl” magazine.
In June 1888 Toumanian fell seriously ill. Ter-Tadevos took his son to the village where he stayed till recovery. He came back only on September 20th.
On December 1, 1888, 19-year-old Hovhannes Toumanian and 17-year-old Mariam Machkalyan marriage took place. A new period began in Toumanian’s life. A few days after the marriage, the rumors about Toumanian’s ordaining a priest were resumed.
Ter-Hovhannes ordained him as a reader in monastery church. That period was short. The daily contacts with the consistory clergy strengthen Toumanian's belief that accepting a spiritual vocation would always connect him with a strange and unfamiliar environment, into which he fell involuntarily and from which he sought to escape.
From November 1889, after Bishop Mambre Sanasaryan became the diocesan leader, the relations between Toumanian and Consistory members got tenser. Abuses and injustices in the Consistory make the poet's verbal and written protests against the “spiritual fathers” more frequent. Toumanian’s conflict with the Consistory atmosphere was reflected in a number of poems he wrote in that period (“My hope had promised me bliss…”, “Why are you mad at an innocent act”, “Prophet”, “To the evil-minded”, “To the simple-minded”, “Azd”, “Again to Them”).
Toumanian didn’t adapt to the new situation and showed the main point of his character – freedom and independence of thought, this made the situation tenser.
In May 1890, he took part in the performance organized on the occasion of the 25th anniversary of Gr. Artsruni’s literary activity, contrary to the Consistory members and not even considering the possible consequence of dismissal.
In January 1892, contrary to the Consistory’s ban and despite being a minor, Toumanian participated in the church deputies’ election.
In addition to those developments, on March 8, 1892, on the occasion of Tiflis diocesan deputies’ election, Toumanian wrote the parody “The March”, where he praised Artsruni and “Mshak” magazine and condemned Bishop Mambre Sanasaryan.
Just a few days after writing the parody, on March 14, 1892, the poet was fired.
In the autumn 1887, when Toumanian had just started serving in the consistory, he got close to Nersisyan school students – Davit Shahlamyan, Aram Arakelyan, Grigor Vantsyan, Arsen Ghltchyan. They created a literary group to fill the Armenian language and literature lessons' shortcomings with self-development. “The Five” had regular meetings and trainings, mostly on Saturdays. It played a big role in Toumanian's literary life.
He yielded to his friends’ claims, and made public his poems’ notebook, the content of which were: “The Dog and The Cat”, “The Moon and The Sun”, “Summer Night in the Village”, “Plow’s Song”, “Old Blessing”, “Maro”, “Alek”, “The Martyr”, “Loretsi Sako” and others.
When the members of the last “Five” got acquainted with their poet-friend’s works, they came up with the idea of publishing Toumanian’s poems in a separate book.
That group of young people could not stay away from the ideological influence of the Armenian national liberation movement, which was on the rise in the late 1880s, by which all the progressive youth of Tiflis were enthusiastic.
The entire Armenian progressive youth of Tiflis was excited about the Armenian national liberation movement, which was on the rise in the late 1880s, and the “Five” youth group could not stay away from that ideological influence.
According to Anoushavan Abovyan, back in 1886-1887 the poet attended secret meetings. According to his wife, Olga Machkalyan, Toumanian was related to Alexander Goloshyan, one of the first figures of the Armenian liberation movement. In 1888 he bought a gun to go to Western Armenia with him, but he fall ill and didn’t leave. In May 1889, they received Galshoyan’s murder news.
Later the poet made a brief autobiographical note – “Revolution.-Galshoyan-Illness…”, which was the approval of his wife’s and An. Abovyan’s evidence.
Thus, the poet's Tiflis life first years can be considered as a period of life experience and impressions enrichment, world recognition, literary and social view formation.