African American adolescents continue to be disproportionately impacted by HIV, sexually transmitted infections (STIs), and unanticipated pregnancies. In-depth, face-to-face interviews among a convenience sample of 32 African American adolescents (16 male and 16 female) were used to explore the reasons why some adolescents decided to engage in sex while others chose to delay sexual debut. Data were analyzed using a thematic analysis. Among the overall sample, psychological motivations, external pressure, physical pleasure seeking, and relationship-related motivations were the major themes cited for engaging in sex by participants and their friends. External support, motivation to avoid negative consequences, not feeling ready or lacking interest in sex, and having negative views about sex were among the major reasons for delaying sex. Several of the emergent themes showed gender differences. Suggestions for future research include the need for sexual education, and STI/HIV prevention programs that are gender sensitive and flexible enough to accommodate multiple factors related to sexual debut.