Peer and dating violence perpetration and victimization are common experiences placing adolescents at-risk for maladaptive outcomes, yet little research has focused on specific problematic situations associated with these types of violence and other related risk-taking behaviors. Further, prevention programs have typically focused on changing beliefs, attitudes, and skill-deficits, with little attention to adolescents’ motivations or perceptions of costs and benefits associated with risky situations, despite support for this type of research in other health-related fields (e.g., substance abuse, behavioral medicine). The current study assessed adolescents’ perceptions of potential positive and negative outcomes associated with risky dating and peer situations, many of which may increase youths’ risks for violence perpetration or victimization. Interviews were conducted with 82 predominantly African American adolescents living in an urban setting. At the conclusion of qualitative coding, 17 and 13 themes were identified for risky dating and peer situations, respectively. Content within these themes included potential positive and negative outcomes and associated processes and contextual factors identified by youth, across topics such as aggression, victimization, and other risks for physical or psychological harm; interpersonal and intrapersonal processes associated with dating and peer relationships (e.g., communication, emotion, respect, pressure); and more concrete costs and benefits for youth (e.g., gain or loss of financial or material goods, opportunities for fun things to do). This research has important implications for improving the ecological relevance and credibility of youth violence prevention programs, and the discussion of decisional balances of potential costs and benefits may represent important targets for prevention programs.