Fifty-seven (57) incarcerated sex offenders were assessed for their capacity to perceive interpersonal difficulties and experience related anxiety. The findings suggest that the men who have sexually transgressed against minors view themselves as easily exploitable and nurturant, and those who have sexually aggressed against adult females demonstrated minimal regard for external negative views of them. These two groups did not differ significantly from each other along social avoidance and non assertiveness dimensions. Assertiveness was found to decrease as a consequence of multiple incarcerations in both groups. Furthermore, perception of interpersonal difficulties and experience related anxiety in our study correctly classified 72% of high and low violent sexual offenders.