1300 students (54.3% girls) 13-16 years old were interviewed in the urban area of Bologna during 2010. Random effect multiple logistic regression models were used. Results show a reciprocal relationship between alcohol use, tobacco, and cannabis. Most users were offered cannabis, began using at 14 years of age, and do not believe using is very dangerous. They live with only one parent, have more than 50 euros of spending money per month, and abuse alcohol, abuse that increases relative to the intensity of cigarette smoking. Legal/illegal dichotomy seems to overturn, where alcohol becomes a "drug" and the use of tobacco, similar to other drugs, is motivated as a solution to reduce anxiety, combat boredom, relax, and to ease loneliness.