Loneliness is one of the problems that is always relevant, attracting not only the attention of scientists and thinkers, but also a wide range of people. The monograph makes an attempt, using philosophical analysis, to rethink the problem of loneliness in terms of aesthetics and ontology. The philosophy of loneliness is essentially the classical philosophy of a free and responsible individual who strives to know himself and not shift the blame for what happens to him to other people, society and God. The philosophy of loneliness is intended to reveal the dramatic essence of human existence, demonstrating different forms of “individual” dramaturgy: ways of recognizing and resolving the contradiction between the external and the internal, “one’s own” and “the other.” The concept of loneliness presented in this study can be defined as philosophical and anthropological. The book is addressed not only to specialists in the field of philosophy, psychology and cultural studies, but also to all thoughtful readers interested in the “mysteries” of the inner world and human subjectivity. The design of the book uses drawings by Arina Snurnitsyna.