The article discusses the method of studying symbolically mediated social understanding in individuals with social maladaptation, within the framework of the cultural historical approach. It has been developed a qualitative-quantitative experimental method of assessing social understanding in adult individuals, taking into account the use of various symbolic forms. The method comprises of 5 tasks. The pilot empirical study involved 70 adult subjects aged between 20 and 40 years old who had committed an offence. The study demonstrated significant difficulties in symbolising and understanding another person’s subjective reality compared to the control group. The study also revealed that individuals with social maladaptation tend to have a distorted understanding of the mental states of others and insufficient “sensitivity” to their symbolic manifestations. Furthermore, the study has revealed significant positive correlations between the results of fulfilling all tasks of the experimental technique.