Following in the footsteps of his colleagues and friends of OBĖRIU, Oleinikov created a personal style of poetry and is considered a versatile author who worked as a poet, journalist, and children’s writer. Furthermore, he dedicated himself to cinema and theatre and developed a passion for mathematics, science and philosophy. This article consists of a concise overview of Oleinikov’s biography and poetry with special focus on a selection of poems dedicated to women. The aim of this article is to draw attention to his epigrams, toasts, and poems in which the author pretends to be a desperate lover or a vain suitor, wearing one of his most famous masks, the heartbreaker, in an ironic and comical treatment of romantic love.