The role of the orbitofrontal cortex in social behavior remains a puzzle. Various theories of the social functions of the orbitofrontal cortex focus on the role of this area in either emotional processing or its involvement in online monitoring of behavior (i.e., self-monitoring). The present research attempts to integrate these two theories by examining whether improving the self-monitoring of patients with orbitofrontal damage is associated with the generation of emotions needed to guide interpersonal behavior. Patients with orbitofrontal damage, patients with lateral prefrontal damage, and healthy controls took part in an interpersonal task. After completing the task, participants' self-monitoring was increased by showing them a videotape of their task performance. In comparison to healthy controls and patients with lateral prefrontal damage, orbitofrontal damage was associated with objectively inappropriate social behavior. Although patients with orbitofrontal damage were aware of social norms of intimacy, they were unaware that their task performance violated these norms. The embarrassment typically associated with inappropriate social behavior was elicited in these patients only after their self-monitoring increased from viewing their videotaped performance. These findings suggest that damage to the orbitofrontal cortex impairs self-insight that may preclude the generation of helpful emotional information. The results highlight the role of the orbitofrontal cortex in the interplay of self-monitoring and emotional processing and suggest avenues for neurorehabilitation of patients with social deficits subsequent to orbitofrontal damage.