The present study explored perceived sexual norms and behaviors related to sexual risk and pregnancy involvement among adolescent males (ages 13 to 20) participating in programs for perpetrators of dating violence. The purpose of this study was to generate hypotheses regarding the contexts and mechanisms underlying the intersection of adolescent dating violence, sexual risk and pregnancy. Six focus groups were conducted (N = 34 participants). A number of major themes emerged: 1) male norm of multiple partnering, 2) perceived gain of male social status from claims of sexual activity, 3) perception that rape is uncommon combined with belief that girls claiming to be raped are liars, 4) perception that men rationalize rapes to avoid responsibility, 5) condom non-use in the context of rape and sex involving substance use, 6) beliefs that girls lie and manipulate boys in order to become pregnant and trap them into relationships, and 7) male avoidance of responsibility and negative responses to pregnancy. The combination of peer-supported norms of male multiple partnering and adversarial sexual beliefs appear to support increased male sexual risk, lack of accountability for sexual risk, and rationalization of rape and negative responses to pregnancy. Further research focused on the context of male sexual risk and abusive relationship behaviors is needed to inform intervention with young men to promote sexual health and prevent rape, dating violence, and adolescent pregnancy.