The paper deals with the challenges that the modern society development faces in social interaction both at the macro level (international interaction, interaction within individual states) and the micro level (the level of interaction in and between small social groups, and interpersonal communication). Social and philosophical understanding of the phenomena of Machiavellianism and manipulative behavior is a relevant issue because in any of the manifestations they are considered as social constructs developing in social interaction, and using philosophical methods and taking into account all the factors influencing them we contribute to their investigation: objective (social) and subjective (psychological). The purpose of the study embraces analysis of different approaches to understand Machiavellianism and manipulative behavior and their evolution from social and political philosophy to social psychology, generalize and develop a more general and complex point of view concerning their essence and determinism. The research methods applied include the philosophical principles of development as the methodological basis to study the issue. These principles cover laws of dialectics: the law of dialectical synthesis, the law of the passage of quantitative changes into qualitative changes, the law of the unity and conflict of opposites; the philosophical principle of determinism; and a systemic activity approach. The main theoretical method used is the content analysis of scientific papers related to the topic of discussion, which allows a comprehensive analysis of the factors associated with the development and manifestation of Machiavellianism and manipulative behavior. The paper analyzes the ideas of Niccolo Machiavelli and his followers, their relationship with the phenomena of Machiavellianism and manipulation, as well as the evolution of these concepts from social and political philosophy considering their global manifestations in politics and the implementation of political power to social psychology studying them in the aspect of interpersonal interaction from the social and philosophical point of view. The criteria underlying the phenomena of Machiavellianism and manipulative behavior are determined on the basis of the system-activity approach. It has been established that the characteristics of Machiavellianism and manipulation (indirect, hidden and implicit influence, deception, disregard of moral and ethical norms and social and cultural values, focus on domination, control, coercion, use of force, use of the other as things, objects, programming of thoughts, intentions, etc.) are the features of public administration sphere, refer to peculiar and interpersonal relations. © 2018, Slovenska Vzdelavacia Obstaravacia. All rights reserved.