In the article the problem of human dialogueness implementation during his educational growth is considered. With the help of research methods, in particular analysis, synthesis, interpretation and reinterpretation, theoretical reconstruction, phenomenological approach and other ways and means of research object and subject comprehension the necessity of higher school’s cultural-educational area dialogization and its transfer to philosophical-metaphysical level have been proven. The content of dialogue use developments in heuristic education has been revealed and its implementation has been done in the philosophical-educational reflexion of cultural-conceptual area of higher school which has to form an innovation person. Philosophical reflexion has made the metaphysical dimension of the dialogue and the tolerance as the constructs of moral-spiritual upbringing and communication which get into the area of sense and high values’ generation. The dialogue is both consequence and a decisive factor of modern dialectic and educational practice quality as well as an ascertained cause of polycultural society which is getting more global features. Representing a human as an object of right protection, declarations, as a free dialogue partner, philosophy suggests introducing specially created (maieutics) communicative scenarios into education. They will encourage education and upbringing and prevent manipulative pedagogical technologies as they have been “recognized” by a person. Determining the role of the dialogue in the conditions of multiculturalism, philosophy proves that the dialogue can be symmetrical and asymmetrical, formal and informal, conflictogenic and tolerant. This fact requires transdisciplinary researches and philosophical-methodological basis of explication of means and mechanisms of human dimension support and value-sense enrichment of real algorithms for the worldview comprehension via dialogical thinking.