Utilizing attachment theory as a basis for conceptualizing close relationships among adolescents, this study investigated two important relationship risk factors (child maltreatment, and adolescent self-perceived insecure attachment style) as predictors of “offender” and “victim” experiences in youth relationships. In addition to considering the influence of these risk factors, we further considered their interaction in predicting conflict in close relationships. Of interest was the extent to which attachment styles may function as a moderator of the relationship between childhood abuse and current abuse in teen close relationships. High school students (N = 321) in grades 9 and 10 completed questionnaires tapping their histories of maltreatment, currently viewed styles of attachment, and conflict in close relationships over the past 6 months. Maltreatment alone emerged as the most consistent predictor, accounting for 13–18% of the variance in male's physically, sexually, and verbally abusive behaviors; in contrast, it was not highly predictive of female's abusive behaviors. Maltreatment was predictive of victimization experiences for both males and females. Attachment style did not substantially add to the prediction of relationship conflict beyond maltreatment; however, avoidant attachment style emerged repeatedly as a significant predictor of female abusiveness and victimization. Attachment self-ratings were found to function as a moderator of child maltreatment in predicting primarily male coercive behavior towards a relationship partner as well as predicting male's experience of coercion from a partner. Thus, the presence of childhood maltreatment and adolescent self-perceived insecure attachment style applies predominantly to male youth. The implication of these gender differences for understanding relationship violence is discussed.