Understanding is an event of intersubjective communication. As an intensional phenomenon, understanding has a certain aspectual form from the perspective of which meaning can be transferred from one participant of communication to another. The monograph provides an epistemological analysis of understanding as a phenomenon of communicability of meaning, the stumbling block of the whole modern philosophical problematics of consciousness. Language games are presented as the intentional content (what do we understand?) of the system of thinking activity in which the subject action forms a single whole with thinking and communication, and different aspectuality (how do we understand?) of the acts of understanding and reflection are organized in a multitude of meaningful interpretations. The enigmas of thinking, rhetorical tropes, stylistic techniques that condition the "miracle of understanding" are considered by the author in the hermeneutic circle of interpretation and social practice. By the example of the means of language thinking the main reflexive mechanisms of socio-cultural dynamics of understanding are revealed. The book is addressed to teachers of humanities disciplines, philosophers, psychologists, literary critics and all those interested in contemporary philosophical thought.