Shaykh al-Islam Yahya is one of the most important representatives of our classical poetry. He used a simple and eloquent language in his poems that he wrote in classical style, and tried to make his words more natural and effective with different preferences which is more suitable for the structure of Turkish, without relying too much on figures of speech. One of these preferences is the intense using of expressions with the subjunctive moods in the poem. In both grammar and rhetoric books, the word is basically divided into two as indicative mood and subjunctive mood. Interrogative, which is one of the parts of subjunctive mood according to the art of rhetoric, appears as an element of style and art in the poems of Shaykh al-Islam Yahya. It is important to analyze all kinds of linguistic performances in detail in classical Turkish poetry, where the style and tone are often more prominent than the content. In this study, all rhetorical interrogatives (all rhetorical questions that have a positive answer) in the Diwan of Shaykh al-Islam Yahya will be classified in terms of meaning and the values that these interrogatives add to the expression in terms of style, poetry and the effect of the word will be examined. These interrogative expressions are not real questions asked with the desire to get answers. In the language of poetry, which is ultimately a fictional text, it is more difficult to determine the meaning and purpose of such metaphorical/rhetorical interrogatives than to determine the meaning and purpose of the interrogatives that arise in other areas of use of the language. For this reason, in this study, it has been tried to reach healthier results by combining the acquis in the rhetoric books with the unique language and conceptual world of classical poetry.