This article describes a preliminary qualitative evaluation of risk and protective factors associated with consistent contraceptive use and healthy sexual decision-making among ten of the first participants in the Prime Time intervention study. Prime Time is an 18-month intervention including one-on-one case management and peer educator training targeting sexually active 13-17-year-old girls who are recruited from health care clinics. Using an approach grounded in findings from previous research, social cognitive theory, and the social development model, Prime Time aims to improve participants' contraceptive use consistency, reduce number of sexual partners, and reduce unwanted sexual activity. Findings from this preliminary evaluation alert health care providers to the complex and dynamic nature of adolescent girls' sexual behaviors and to a broad range of risk and protective factors within individuals and their environments that may influence adolescent girls' sexual behaviors and contraceptive use. Findings suggest that an ongoing, supportive relationship with a case manager who is able to pace and tailor an intervention to the individual young person can have positive effects on adolescent girls' sexual behaviors and contraceptive use.