The article views personal peculiarities of city and countryside teenagers. It presents the result of the empiric investigation, which was carried out on a sample of city (n = 620) and countryside (n = 580) teenagers (aged 12–18) with application of the following psychodiagnostic tools: questionnaire regarding change of aggressive and hostile reactions (Buss-Durkey Inventory), E. S. Romanova’s questionnaire of emotional strain; State-Trait Anxiety Inventory – STAI by Spielberger and Khanin, L. D. Moionova’s scale of asthenic reaction, The Giessen Subjective Complaints List. It is shown that specific complexes of personal characteristics are being formed under various socio-cultural conditions. City teenager’s reaction to the surrounding environment is expressed through formation of stable forms of different types of tiredness and the increase of hypochondria (complaints about state of health, sometimes without any objective traits of the disease). Countryside teenagers adapt to the environment through formation of high levels of anxiety and aggressiveness. Offence dominates in countryside male teenagers, while the Feeling of Guilt is predominant in countryside female teenagers. The applied aspect of the problem under study can be implemented in the development of programs of psychological and educational support programs for teenagers.