Psychopathy is a severe personality disorder marked by a wide range of emotional deficits, including a lack of empathy, emotion dysregulation, and alexithymia. Previous research has largely examined these emotional impairments in isolation, ignoring their influence on each other. Thus, we examined the concurrent interrelationship between emotional impairments in psychopathy, with a particular focus on the mediating role of alexithymia. Using path analyses with cross-sectional data from a community sample (N = 315) and a forensic sample (N = 50), our results yielded a statistically significant mediating effect of alexithymia on the relationship between psychopathy and empathy (community and forensic) and between psychopathy and emotion dysregulation (community). Moreover, replacing psychopathy with its three dimensions (i.e., meanness, disinhibition, and boldness) in the community sample revealed that boldness may function as an adaptive trait, with lower levels of alexithymia counteracting deficits in empathy and emotion dysregulation. Overall, our findings indicate that psychopathic individuals’ limited understanding of their own emotions contributes to their lack of empathy and emotion dysregulation. This underscores the potential benefits of improving emotional awareness in the treatment of individuals with psychopathy.