Background: Teen dating violence (TDV) is a growing issue among adolescents, leading to several negative behavioral and psychological consequences. Most studies have been carried out in North America, whereas few have been conducted in Europe and Italy. Despite the existence of some studies underlying risk factors for TDV, to the best of our knowledge, none of them have tested a comprehensive model that includes several risk factors (and their interplay) for verbal–emotional and physical TDV such as witnessing IPV, involvement in school bullying and victimization, cyberbullying and cybervictimization, deviant behaviors, and violence against teachers. Methods: A short-term longitudinal study involving 235 students aged 10–14 who filled in an online questionnaire twice. Results: The tested path analysis model showed an excellent fit to data, with a different pattern of risk factors affecting youth involvement as perpetrator and victim in physical and verbal–emotional TDV. Differential paths emerged for females and males. Conclusions: This article includes discussions on practical and policy implications for future research, stressing the need to develop, implement, and evaluate the effectiveness of primary prevention programs addressing and managing youth involvement in violent and aggressive behaviors.