Based on classical novels, there is covered the issue of categorization of emotive concepts in the process of communication. On the basis of the suggested criteria of types of categorical emotive situations there are analyzed the communicative situations in which craftiness becomes a dominant strategy of one of speech partners.

Emotional concepts insidiousness and guile are described in the diachronic aspect, which supposes the etymological analysis, and in synchronistic aspect understood as representation in the modern world picture, which is found out through investigation of the basic components of the concepts.