The Triarchic Psychopathy Model proposes that psychopathy encompasses three distinct phenotypic constructs: disinhibition, meanness and boldness. Unlike the other two, boldness can be viewed as an adaptive component of psychopathy, and can be useful for identifying “successful“ psychopathy. Therefore, the aim of this study was to explore the relationships between boldness and different prosocial and antisocial criteria (empathy, impulsiveness and aggression) and whether boldness predicts these outcomes above meanness and disinhibition. Data was collected on 600 students (292 female) from various faculties in Zagreb, using the Triarchic Psychopathy Measure (Patrick, 2010), Interpersonal Reactivity Index (Davis, 1983), The Barratt Impulsiveness Scale–11 (Patton et al., 1995), and Reactive–Proactive Aggression Questionnaire (Raine et al., 2006). Results showed that boldness was associated with some adaptive tendencies. However, it was also associated with some maladaptive tendencies, indicating that it cannot be conceived of as a purely adaptive expression of psychopathy.