The article analyzes certain socio-cultural and personal predispositions, which determine the modern diversity of displays of subjective uncertainty and ambiguity. The importance of understanding the relations between the resourceful and the psychopathological aspects of the ambiguity phenomenon and the cultural environment with its destructive ideals and mythologems, manipulative media-technologies and all-pervading idea of deconstruction is stressed for the creation of “realistic clinical psychology” (in terms of A.R. Luria). Methods for modeling the experiences of ambiguity in experimental settings, in pathopsychological examination and in projective psychological diagnostics are put in comparison. The arguments are adduced for the interpretation of deficient manifestations of subjective uncertainty and ambiguity as a criterion for diagnostics of the severity of personality disorder.