The purpose of the present study is to determine if high school students' character strengths composed of twenty-four different strengths, virtues including six dimensions and demographic characteristics predict risky behaviors. The participants of the study were 380 students aged between 14-19 years and enrolled in general high schools. The data was collected by using the Values in Action Inventory of Strengths for Youth and the Risky Behaviors Scale. From the findings, it was determined that the risk of school drop-out score was higher in the ninth grades and the male students had more risky behaviors compared to their female counterparts. Moreover, it was also determined that the risky behaviors were significantly related to many character strengths. Besides this, as a result of the regression analyses, it was found that the character strengths predicted risky behaviors composed of the areas of anti-social behaviors, use of alcohol/cigarette, eating habits, suicide tendency and school dropout at different levels. The findings were discussed within the context of adolescents' psychological counseling needs and suggestions were proposed.