Multinomial logistic regression was applied to data comprising 432 adolescents’ self reports of engagement in risky behaviors. Results showed that gender, intention to drop from the school, family structure, self-esteem, and emotional risk were effective predictors collectively. Three methodological issues were highlighted: (1) the use of odds ratio, (2) the absence of an extension of the Hosmer and Lemeshow test for multinomial logistic models, and (3) the missing data problem. Psychologists and educators can utilize findings to plan prevention programs, as well as to apply the versatile and effective logistic technique in psychological, educational, and health research concerning adolescents.