The purpose of the present study was to increase our understanding of the relations among embarrassment, Theory of Mind (ToM), and emotion dysregulation in adolescents with Asperger's Syndrome and High Functioning Autism (AS/HFA), topics that have not previously been the foci of research in this population. The research sample consisted of 42 participants, split equally between adolescents with AS/HFA and typically developing (TD) adolescents. Participants with AS/HFA were matched with TD participants for chronological age and gender. Parents of all participants, typically mothers, were also required to complete measures. Participants were presented with vignettes of embarrassing or anger inducing scenarios, following which they were asked to provide ratings indicating the degree to which they would be embarrassed or angry in the protagonists' positions. Next they were asked to justify those ratings. Results indicated that the AS/HFA group experienced greater difficulty than the TD group with measures requiring ToM abilities. This was particularly true of embarrassment/social faux pas situations. In contrast, both groups performed similarly on measures involving anger-inducing situations that require less ToM. The significant difficulty of the AS/HFA group in understanding ToM in embarrassment measures was corroborated by their poor performance on an independent ToM measure. In addition to having significant difficulty in understanding embarrassment, the AS/HFA group was significantly less able than the TD group to recount personally embarrassing experiences. Regarding emotion regulation, participants with AS/HFA were significantly less able than their TD peers to regulate their emotions through reappraisal. Similarly, parents of the AS/HFA participants reported a significantly higher level of emotion dysregulation in their children than did the parents of the TD participants. Further, participants with AS/HFA had a significantly higher utilization frequency of negative strategies than their TD peers when embarrassed, which aligned with parent report. Negative strategies included internal, verbal, and physical self-injurious behaviors, as well as destructive interpersonal behaviors, e.g., falsely accusing, yelling at, or hitting others. These findings emphasize the critical and potentially harmful impact of embarrassing experiences in the daily lives of adolescents with AS/HFA.