Sex-offenders are at risk of criminal recidivism. For the treatment to be truly effective, it must be individualized. For this purpose, an accurate assessment should focus on criminological, psychological, and psychopathological features. The present study compared sex offenders with other offenders on historical experiences (i.e., problems with violence, anti-social behaviors, problems with personal relationships, problems with substance use, traumatic experiences, and parenting style). In addition, given the association between life events and psychopathy, we explored whether the relation between life events and crime type (sexual crime vs. other types of crime) might be moderated by psychopathy traits (interpersonal and affective deficits and antisocial behavior). Eighty-eight sex offenders (76% of whom child molesters) and 102 other offenders were included. The Historical, Clinical and Risk Management - 20 item Version 3 (HCR-20V3) and Psychopathy Checklist-Revised (PCL-R) were administered. The scores of the HCR-20V3 Historical scale items were computed to assess life events. The scores of the PCL-R factors, F1 Interpersonal affective deficits and F2 Antisocial behavior, were recorded. The presence of a history of problems with non-intimate relationships was the only significant risk factor for sexual crime compared with other crimes. Interpersonal and affective deficits provided an increased likelihood of being sex offenders as compared with other offenders when problems with non-intimate relationships were possibly/partially or certainly present.