Objective: This exploratory study examines the reported dating violence and its association with sexual risk behavior among Israeli adolescents, who are at risk for dropping out of school. Methodology: A convenience sample of 105 at-risk youth (51 boys and 54 girls) completed self-administered anonymous, questionnaires in small same-gender groups. The questionnaire included a Hebrew version of the Conflict in Adolescent Dating Relationships Inventory, a valid scale developed in the US especially for adolescents, the Hebrew version of the Conflict Tactics Scale and the Self-Efficacy to Refuse Sexual Behavior Scale. Results: We found high rates of perpetration of verbal-emotional abuse for both girls and boys. Rates of reported victimization by physical abuse were higher among boys but that by sexual abuse were higher among girls. We found a moderate inverse association between victimization by dating violence and practicing safe sex among girls. There was a similar but much stronger association for boys who were victims of dating violence. Conclusions: The high rates of various types of dating violence in Israel, at least among at-risk adolescents, should raise concern and motivate designing and implementing specific prevention interventions. The high reported rates of victimization from dating violence among boys are somewhat surprising and call for special attention and more indepth studies.