Abstract: This article is dedicated to a comparative analysis of two works by M. Y. Lermontov, which represent the interpretation of the common biographical context. The subject of this research is the specificity of transformation of the biographical fact into the artistic generalization in the works of M. Y. Lermontov. The object of this research is the drama "Two Brothers" and the novel Princess Ligovskaya” viewed within the paradigm of artistic comprehension of the scenario of unfaithfulness, or destruction of love as conceptually important in the conflict present in the works of M. Y. Lermontov. Such approach, based on interrelation between the creative and biographical, allows making important remarks on specificity of the phenomenon of autobiographism in the works of M. Y. Lermontov. The author analyzes the initial biographical situation (relationship between Lermontov and V. A. Lopukhina), and concludes that two literary texts – drama and novel – represent a distinct system of creative reflection of the biographical fact. It is established that in the process of creating the drama, and the novel later on, Lermontov ensues the need for artistic interpretation and resolution of the situation of unfaithfulness as an instance, and in a broader sense – as an ontological pattern; however, the conflict cannot be settled within the framework of this storyline. Since 1837, autobiographism in Lermontov's works ceases to play the crucial role; in other words, personal situation and its artistic interpretation no longer coincide, which renders impossible to continue the novel. Such circumstance allows realizing the reasons of incomplete works of Lermontov’s early period, which lie in inability to resolve love conflicts with a positive finale.