Background and objectives: Today, one of the most significant social ills among adolescents is the emergence of risky behaviors. The current article is aimed to investigate the causes of tendency to risky behaviors among male high school students in the city of Tehran.Methodology: The research is qualitative and data were gathered via semi-structured interviews. Responses given by students were recorded and were brought on paper and they were analyzed by way of content analysis. Then, the data were categorized via open and pivotal coding procedure. From among students with problems risking being expelled, the number of 20 students was selected as the sample size.Findings: Factor were divided in two general categories; 1) individual factors of students and their needs: pleasure-seeking, curiosity gaining identity, false self-confidence and 2) background factors: contact with peers, entertainment with mobiles, wandering in virtual spaces, easy and cheap access to kinds of material, feasts and mixed parties, negative model-taking, lack of sports and entertainment spaces, parents' unawareness, labeling, and financial limitations. As well, the students were wishing for becoming wealthy and communication with the opposite sex.Conclusion: Research findings showed that the interviewed had not learnt necessary skills for dealing with their own needs and wants and paid no attention in their own behaviors to their consequences. It is thus imperative to prioritize necessary training for this age group.