Objective: The research aims to investigate family communication regarding sexuality and the possible link between insecure attachment, violence in relationships, and the tendency toward sexual sensation-seeking in a sample of Italian sexual offenders. Design and method: We evaluated 29 male sexual offenders in two correctional facilities of Southern Lazio (Italy) (mean age = 40.76; SD = 11.16). The participants completed general questions about their family and sexual education and fulfilled the following questionnaires: Compulsive Sexual Behavior Inventory (CSBI), Sexual Sensation-seeking Scale (SSSS), and the High-Risk Situation Checklist, adapted in Italian, as well as the Attachment Style Questionnaire (ASQ), validated in Italian. Results: Most of the participants had never talked about sex within their family and perceived a severe or abusive education during childhood. In addition, positive correlations emerged between SSSS and the two scales of the CSBI, as well as between insecure attachment style, CSBI, and sexual sensation-seeking. The participants also reported some critical issues regarding the personal perception of high-risk situations linked to sexual relapse. Conclusions: The data suggest factors to investigate, such as family education and relationships and the personal perception of sexual recidivism. The results might be effective in treatment and prevention programs among sex offenders.