The methodological research basis and the description of generation community mentality features are presented to create prerequisites for understanding optimization and broadening of dialogic generational communications. The main directions of the research are identified and substantiated. They are determination of the informational and meaningful foundations of generational mentality, the sample characteristics as for its social, cultural, historic area, peculiarities of social and psychological differences in generational habits and social positions (entelechies). According to the formed criteria of differentiation and functional boundaries between generations, three generations of Children, Parents, and Grandparents are singled out as a result of clustering array of the experimental data. The features of the social and psychological differences in habits and social positions (entelechies) of generations are analyzed. The determined generalized characteristics of the mental systems of generation communities allowed us to confirm assumptions about uniqueness and influence of relationships delivery of the mental features of generation communities, formed under influence of historical events.