The purpose of this study was to examine qualitatively the context of and reasons for condom use and non-use among adolescent male perpetrators of dating violence. Semi-structured anonymous interviews were conducted with 19 adolescent males recruited from intervention programs for adolescent perpetrators of dating violence. Interviews included questions about dating violence perpetration, sexual relationships and risk behaviors. Interviews were analyzed using a content analysis approach and coded to examine boys' condom use and non-use behaviors and contexts. Participants (n=19) were aged 17-21 years and were predominantly white (n=9; 47%) or black (n=4; 21%). Half (n=10; 53%) indicated four or more sex partners in the past three months; half (n=10; 53%) reported no or inconsistent condom use in the past three months. Qualitative findings from this study revealed condom use in high-risk casual sex encounters, including 'trains' (1-2 girls having sex with several boys sequentially). Non-use of condoms was more common in steady, often abusive, relationships, although boys reported sexual infidelity in these relationships. These results indicate that non-use of condoms is occurring among adolescent male perpetrators of dating violence, particularly in the context of their steady relationships and despite reports of very high risk sexual activity including sexual infidelity, involvement in 'trains' and multiple sex partners. Sexual health interventions integrated with dating violence and sexual assault prevention efforts and tailored to adolescents are needed.