While the prevalence of teen dating violence (TDV) is among the highest for African Americans (AA), the research and narrative surrounding this issue has been historically one-sided. This qualitative study was conducted to further explore the candid perspectives of adolescent AA males regarding healthy and unhealthy dating relationship dynamics. Convenience sampling and snowball sampling were utilized to recruit 19 AA males from schools and community youth groups around the greater Washington DC area. Semi-structured in-depth interviews were conducted. Analysis consisted of open coding, sorting, aggregation and synthesis of responses to the guiding question question: “How would you describe a dating relationship that was unhealthy or harmful?” Narratives provided multi-layered, descriptive characterizations of healthy and unhealthy dating dynamics. Through an iterative process, emergent themes and sub-themes were generated. The five emergent themes were: Amiss or Dissed Communication; Distrust, Dishonesty, Disloyalty; Fighting and Poor Conflict Resolution; and, Abuse. Adolescent AA males displayed a strong awareness of what constitutes unhealthy dating relationship characteristics, especially concerning conflict and abusive behaviors. Characterizations that addressed Communication and Distrust, Dishonesty, and Disloyalty may present areas that should be focused on in future prevention efforts. Prevention and intervention programs aimed at decreasing TDV within the African American community will benefit tremendously from these authentic perspectives. By building off of the knowledge and values already expressed among adolescent AA males, rather than perpetuated stereotypes, programs will more effectively connect with, educate, and empower them to build healthy dating relationship dynamics.