Hume and Smith advance different answers to the question of whether sympathy can ever be the foundation of the moral order. They hold contradictory views of sympathy, called here ‘the Fellow-Feeling Paradox’. For Hume, fellow-feeling tends to reverberate in society, leading to the socialization of the individual and even mob (collective) psychology. Hence, sympathy cannot be the foundation of the moral order. In contrast, for Smith, fellow-feeling develops into critical judgment of the emotions/actions, leading to individual moral autonomy even self-command. Hence, sympathy can be the foundation of the moral order. This paper provides a resolution of the two answers.