Psychopathy is characterized by deficits in affective and interpersonal functioning. Neglecting social reinforcements that are typically attained through the experience of empathy, which is lacking in people with high levels of psychopathy, results in lack of awareness of the other person’s distress and, in turn, perceived lack of ‘caring’ emotions. Still, some research suggests that people with psychopathy do experience negative emotions more strongly in youth, resulting in the development of unhealthy coping mechanisms to manage. It was hypothesized that the relationship between decreased empathy and increased psychopathy would be mediated by increased distress tolerance. It was also hypothesized that as levels of psychopathy increase, emotions like sadness and anxiety would decrease, while anger would increase and happiness would remain relatively stable. Participants, totaling 180, completed 5 questionnaires assessing distress tolerance, psychopathy, empathy, emotional experience, and beliefs about the functionality of emotions. Although empathy and distress tolerance were found to be significantly correlated with the interpersonal manipulation facet of psychopathy, the mediation was not significant. Total psychopathy was not significantly correlated with distress tolerance or any emotional experiences. These findings suggest that further research in this area should examine how more specific components of these variables uniquely contribute to psychopathy.