It has been suggested that child sexual abuse is related to poor attachment to parents, which is associated with an inability to form intimate relationships. Seto and Lalumière indicated that there were too few studies of adolescent males to determine whether poor attachment was associated with perpetration. This study was designed to follow up on a previous study and further explored the association between insecure attachment to parents, social isolation, and interpersonal adequacy to child sexual abuse perpetration in adolescents. We compared two samples of adolescent males who had committed sexual offenses, those who committed offenses against children (n = 140) and those who committed offenses against peer or adults (n = 92), with a sample of similarly aged males in treatment for mental health or substance use issues (n = 93). Data were collected using a semi-structured interview and computer-administered questionnaire. We found an indirect association between anxious attachment and sexual offenses against child victims, which was accounted for by measures of social involvement and social isolation. These involvement and isolation measures also did not have a direct association with sexual offenses against child victims, in that their contribution was accounted for by a measure of Masculine Adequacy. This Masculine Adequacy, combined with decreased levels of Sexual Preoccupation and Hypersexuality and increased Sexual Compulsivity, was associated with commission of child sexual abuse. The interpersonal variables did not enter a model predicting sexual offending against peers/adults, which seemed solely associated with the interaction between Sexual Compulsivity and Hypersexuality.