Analysis of psychological literature suggests that among modern children, role-playing games are undergoing major changes in the temporal and spatial dimensions, yet remain relevant for their development, including socialization. The study aims to examine the characteristics of role-playing games as a factor in the socialization of modern preschool children in the cultural space of a provincial city. The utilized empirical methods include a verbal survey of the teachers of senior and preparatory kindergarten groups and observation of children in play activities. Analysis of the study results shows that: 1) many modern parents consider early, accelerated learning of children to be a much more important childhood activity than play without taking seriously the consequences of such underplaying, such as the difficulties in socialization; 2) children often do not want to organize role-playing games themselves, giving their preference to gadget-based recreational activities, which often satisfies adults who get extra free time for their urgent matters; 3) the themes and plots of games predominantly reflect the everyday and virtual (the content of television shows and computer games) sides of life while professional and social scenarios are less represented; 4) kindergartens predominantly have fixed play corners “for boys” and “for girls” and offer closed realistic toys with a fixed mode of action, which encourage children to stereotypical and monotonous actions; 5) substitute items, which develop imagination, fantasy, and creative thinking, are typically not used by modern preschool children in play; 6) there are pronounced gender differences in children’s play interests, which are most striking in rural areas, in small provincial towns; 7) teachers may project their perception of the game onto its plot, thus suppressing some independence of children.