The study of suicidal risk has increasingly emphasized the importance of assessing specific suicidal motivations. Motivations express an elaboration of the condition of psychache, representing an effective perspective on the management of suicidal risk in psychotherapy. This study explores suicidal motivations and personality pathology in a clinical sample of adolescents with suicidal ideation or a history of suicide attempts. We aim to investigate how specific motivational factors and personality disorders (PDs) contribute to the foreseeability of suicidal outcomes, such as the occurrence, number, and lethality of suicide attempts and their interaction with the impact of personality disorders. A sample of 134 adolescents aged 12-18, with active suicidal ideation or recent suicide attempts, was assessed using a combination of self-report measures and structured clinical interviews. Binomial logistic regressions and linear regressions were conducted to explore the predictive value of PDs and motivational factors on suicidal behaviors. The results indicate that specific suicidal motivations, such as interpersonal influence, escape fantasy, and absence of fear, provide an additional increase in the foreseeability value beyond personality disorder criteria alone. These findings suggest that assessing suicidal motivations can significantly enhance risk evaluation and inform more effective therapeutic interventions. Beyond identifying certain risk factors, the therapist’s ability to diss and process specific suicidal motivations in the context of the therapeutic relationship can be a decisive factor in monitoring and directly intervening on the risk.