This qualitative study focused on the identification of problem situations associated with adolescent dating experiences and relationships, including those that placed youth at risk for dating violence perpetration or victimization. Interviews were conducted with 44 African American middle and high school students in an urban school system. Qualitative analysis identified 18 individual themes representing six categories of problem situations: (a) approach and initiation; (b) conflict, conflict resolution, and break-ups; (c) communication, connection, and emotion; (d) aggression and victimization; (e) the role of others; and (f) media and technology. Identification of these problem situation themes has important implications for developing and evaluating prevention efforts designed to foster healthy adolescent dating relationships.