Attachment deficits have been suggested as an etiological explanation underlying the development of sexually abusive behaviors and general delinquency among youth. Yet, few researchers have explored the discriminating functions of attachment characteristics or investigated attachments as a stand-alone risk/protective factor explaining offending profiles among youth sexual offenders. This article explored the differences in characteristics of parental and peer attachments between youth sexual (n = 355) and non-sexual offenders (n = 150). Furthermore, associations between family and peer attachments and criminal profiles of sexual offenders were tested. The t-test results revealed that the groups of youth differed on various mother and father attachment characteristics, with youth sexual offenders exhibiting greater deficits. Regression models revealed lower levels of mother and peer trust and communication were associated with more severe sexual offenses; low levels of mother trust were associated with more victims; and low levels of mother trust and high father alienation were associated with more non-sexual criminality. Practice implications suggest the need to amalgamate families more consistently into treatment and addressing peer dynamics within groups and community contexts.