The article is devoted to the study of philosophizing as questioning. It is substantiated that in terms of content, it is, firstly, an ideological questioning about the world and the place of human in it; secondly, conceptual questioning, which is realized in a developed philosophical theory; thirdly, metaphysical questioning, the purpose of which is the knowledge of being as such; fourth, transcending questioning, expanding and complicating the spheres of knowledge and practice; fifth, projective questioning aimed at creating and implementing possible (...) models of a person; sixth, personal questioning, which forms the consciousness of a particular individual. Various types of philosophizing in ancient, medieval, modern European and modern thought are analyzed. It is emphasized that the definition of the main issue of philosophy as the question of the relationship of thinking to being, spirit to nature makes sense only within the framework of classical thought. In post-non-classical philosophy, interrogation is carried out within disparate semantic "clusters", through which it is impossible to comprehend the being as such, to cognize the world whole. (shrink)