This paper discusses the relationship between philosophy and literature, their mutual entanglements, differences and similarities. The aim of the article is to reflect on the different concepts presenting the relationship between these two discourses. The first position claims that philosophy and literature are separate, while the second one blurs the boundaries between them. The latter view has two versions: one that claims to diminish the separateness of the discourses in the name of meaning or indication, and another that accentuates their (...) internal entanglement, which could be described in terms of two phenomena – the literary nature of philosophy and the philosophical nature of literature. Further issues discussed are existential philosophy as a special example of the coincidence of literature and philosophy, and the philosophy of literature as a discipline exposing, among other things, the philosophical nature of literature on top of the philosophical and methodological foundations of its studies. Classical works by Plato and other ancient Greek philosophers, the works of Roman Ingarden, John Austin, Tadeusz Komendant, Albert Camus, and Martin Heidegger are interpreted. The analysis of these works is confronted with the reading of such writers as Fyodor Dostoyevsky, Franz Kafka, Herman Hesse, Witold Gombrowicz and Tadeusz Różewicz. The article is a theoretical inquiry and fits into the discipline which is called the philosophy of literature. The author adopts a hermeneutical perspective, noting, however, that hermeneutics is not a method in the strict sense. The text posits that philosophical and literary discourse are mutually entangled, despite the fact that historically the separateness of the two orders has often been emphasized. (shrink)