In this study, we investigated whether differences in the experience of regret may be a potential explanation for damaging behaviours associated with psychopathy and criminal offending. Participants were incarcerated offenders (n = 60) and non-incarcerated controls (n = 20). Psychopathic traits were characterised with the Psychopathic Checklist: Screening Version. Regret was assessed by responses to outcomes on a simulated gambling task. Incarcerated offenders experienced a reduced sense of regret as compared to non-incarcerated controls. We obtained some evidence that specific psychopathic factors and facets could differentially relate to the experience and use of emotions. Our data provide initial evidence of important associations between negative emotions and decision behaviour in the context of criminal offending.