Two mental disorders seem to differ dramatically in terms of social fear and characterizing behavioural tendencies: social anxiety (SA) and psychopathy (PP). SA is characterized by high fear in social situations and avoidance behaviour. PP, on the other hand, is characterized by a lack of fear and risk-taking, aggressive behaviour. While SA is the most prevalent anxiety disorder, PP is less common though related to high societal costs. In this research, the (dis)similarities between SA and PP will be examined in terms of cognitive biases, behavioral tendencies and emotional experiences. In order to do so, self-reports, biological assessments, experimental tasks and longitudinal data are used. Studying SA and PP in unison will improve our current understanding of the mechanisms underlying problematic social behavior, which might eventually inform clinical practice and open up avenues for enhanced diagnostic and treatment approaches.