We explored the interrelationships between risk-taking and self-harm in typically developing adolescents by examining various contributing factors, such as personality traits, difficulties in emotion regulation, attachment styles, and maladaptive psychological functioning. A sample of 234 Italian adolescents completed the Risk-Taking and Self-Harm Inventory for Adolescents (RTSHIA), the Risk-Taking Questionnaire (RT-18), the Difficulties in Emotion Regulation Strategies (DERS), the State Adult Attachment Measure (SAAM), and the Youth Self-Report (YSR). Network analysis was used to visualize and describe the interdependencies among the variables. Risk-taking behaviors were strongly linked to rule-breaking, aggression, and risk propensity, while self-harm behaviors were connected to limited access to emotion regulation strategies and thought problems. Centrality indices indicated that variables such as anxiety/depression, limited access to emotion regulation strategies, and rule-breaking had a high influence within the network. This study provided a comprehensive understanding of the nomological network of risk-taking and self-harm behaviors among adolescents. It highlighted the relative importance of factors such as emotion regulation difficulties and maladaptive psychological functioning in influencing these behaviors. The findings could inform psychological interventions and prevention strategies targeting adolescents at risk for engaging in risk-taking or self-harm behaviors.