Individuals with psychopathic traits often demonstrate blunted reactivity to negative emotional stimuli. However, it is not yet clear whether these individuals also have difficulty regulating their emotional responses to negative stimuli. To address this question, participants with varying levels of psychopathic traits (indexed by the Triarchic Measure of Psychopathy; Patrick, 2010) completed a task in which they passively viewed, increased, or decreased their emotions to negative picture stimuli while electrocortical activity was recorded. During passive viewing of negative images, higher boldness, but not higher disinhibition or meanness, was associated with reduced amplitude of the late positive potential (LPP), an ERP that indexes reactivity to emotionally relevant stimuli. However, all participants demonstrated expected enhancement of the LPP when asked to increase their emotional response. Participants did not show expected suppression of the LPP when asked to decrease their emotional response. Contrary to the electrophysiological data, individuals with higher boldness did not self‐report experiencing blunted emotional response during passive viewing trials, and they reported experiencing greater emotional reactivity relative to other participants when regulating (e.g., both increasing and decreasing) their emotions. Results suggest inconsistency between physiological and self‐report indices of emotion among high‐bold individuals during both affective processing and regulation.