The sense of emptiness is still a poorly defined construct in the literature, yet it is frequently reported in individuals with borderline personality disorder, depressive symptoms, and narcissistic personality disorder. This paper aims to replicate those research studies showing that there are significant correlations between emptiness, insecure attachment styles, maladaptive childhood experiences, shame, impulsivity, depression, and borderline and narcissistic personality features. Additionally, it was hypothesized that a significant correlation would exist between the sense of emptiness and burdening guilt and self-hate, and that self-hate would mediate the relationship between adverse childhood experiences and preoccupied attachment and sense of emptiness. The sample consisted of 128 Italian participants recruited online, who completed a battery of self-report questionnaires designed to measure the psychopathological features described above. The sense of emptiness was strongly correlated with depression (rho 0.81, p<0.001), borderline personality traits (rho 0.59, p<0.01), and narcissistic vulnerability (rho 0.39 p<0.01). Additionally, it was correlated with adverse childhood experiences (rho 0.39, p<0.01), interpersonal problems (rho 0.41, p<0.01), shame (rho 0.54, p<0.01), and interpersonal guilt. Burdening guilt and self-hate mediated the relationship between adverse childhood experiences and preoccupied attachment on one side and the sense of emptiness on the other. The study confirms the correlation between the sense of emptiness and psychopathology, particularly with personality disorders and depression. Additionally, the study identifies interpersonal guilt, particularly self-hate and burdening guilt, as factors correlated with the sense of emptiness and mediating the relationships between adverse childhood experiences and preoccupied attachment with the sense of emptiness.