Risky adolescent behavior represents a significant public health concern, with potential detrimental consequences for youth and society in general. Problem behavior theory suggests that engaging in one type of problem behavior increases the likelihood of other problem behaviors. As a result, understanding how youth perceive common dating risk situations that may place them at risk not only for dating violence but also for a variety of other problem behaviors could inform prevention programming. Using qualitative interviews with 43 urban, predominantly African American adolescents, we assessed risk perceptions via youths’ identification of potential positive and negative outcomes associated with dating situations that may place teens at risk for negative outcomes including violence and risk behaviors. Six themes each of potential positive and negative outcomes emerged, including positive themes related to interpersonal skills, relationship connections, having fun, and improving image, and negative themes related to victimization, control, jealousy, conflict, consequences, and reputation. This research has important implications for youth prevention programs, especially those focused on helping adolescents develop healthy relationships.