Background: Empirical studies and clinical approaches have evidenced that the suicidal process is not a simple outcome of specific pathological risk factors that trigger suicidal ideation and eventual conducts. Indeed, specific suicidal motivations can be identified that activate and sustain the emergence of suicidal ideation and its possible development into suicidal planning and attempt. The creation of specific suicidal motivations should be studied as an active attempt to deal interpersonal issues and regulate the emotional dynamics that may assume a particular weight in patients with personality pathology. Such interpersonal and emotional issues come to the forth in the meaningful relational context of the therapeutic relationship. In the present case study we propose to illustrate the clinical congruence between suicidal motivations as they emerge through the analysis of the therapeutic exchanges in the context of treatment of two adolescents, respectively diagnosed with narcissistic and borderline emerging personality patterns. Method: Two adolescents, named Harold and Jade, who attempted suicide multiple times, were assessed using the Psychodiagnostic Chart Adolescent (PDC-A) of the Psychodynamic Diagnostic Manual-Second Edition (PDM-2) to evaluate their mental functioning, personality pathology, and symptoms patterns. Moreover, the therapist were asked to assess the patient’s suicidal motivations through the Motivational Interview for Suicide Adolescents (MIS-A) relying on the patients’ comunication within the therapeutic context and to identify specific patterns of interactions that were highly significant representatives of the type of therapeutic exchanges preceding and following their suicide attempts. Results: The results of Harold and Jade’s assessment showed how different emerging personality patterns shape the patients’ suicidal motivations. Harold presented a narcissistic emerging personality pattern characterized by the need to deny and cover his vulnerabilities through escape suicidal fantasies and triumphant control over the meaningful others, including the therapist. In contrast, Jade presented a borderline emerging personality pattern characterized by the use of suicide attempts to express her inner and unspeakable pain and cry for help along with a sense of estrangement from relationships. Conclusions: The active analysis of the therapeutic exchanges may help the therapist to identify the meaning shaping suicidal motivations and has important implications for the therapeutic process of adolescents with personality disorders and the understanding of their risky behaviors.