An adolescent’s knowledge of him/herself (positive aspects and weaknesses) is shaped by interactions with external and internal factors, including the family context and the educational environment. The assessment of this knowledge serves to construct the concept of self-esteem. The main objective of the present study was to examine the prevalence of self-reported emotional and behavioral symptoms in a representative sample of Italian adolescents and their relationship with gender and age, using Goodman’s Strengths and Difficulties Questionnaire (SDQ). A total of 440 adolescents (49.8% female) aged 15–18 years from the southern Italy region participated. The results show the prevalence of emotional and behavioral symptoms in the analyzed sample. Gender differences were also found in the variables under study. In conclusion, the SDQ test is offered as an agile, simplified, and effective tool, to be proposed to all formative agents who are concerned with the interest and care not only of young people, but also of the future of socio-political realities.