In this work are submitted the data of the homeless (living in the streets, shelters and boarding schools) and people having a living space (working people and pupils from the secondary schools), with the purpose of the analysis of homeless personality especialies. Personality especialies – motivation to study, self – esteem, values and psychological filling. 340 men participated in the research. From them 176 are homelesses (126 teenagers living in the boarding schools and 50 middle adult people living in the shelters and in the street ). The teenager‘s age was from 12 to 18 years old. Middle adult age people were selected from 34 to 60 years old ( By Barbara & Philip Newman). With the purpose to analyze homeless personality especialies, such as hypotheses and tasks were put forward (which subsequently have proved to be true): 1. The itself estimation of the middle adult age homeless is lower, than at the same age working people. 2. The value of the middle adult age homelesses and working people of the same age are different. 3. To compare personality especialies of homeless teenagers and secondary school pupils (motivation to study, self – esteem, values and psychological feelling). 4. To compare personality especialies of the middle adult age homeless and the same age working people (motivation to study, self – esteem, values and psychological filling). 5. To compare personality especialies of homeless teenagers and the middle adult age homeless (motivation to study... [to full text]