This two-phase, community-based pilot study examined the impact of an innovative calendar-based assessment on HIV risk perception and risk reduction planning with racially diverse youth aged 14 to 21 at a public health clinic. Participants (N = 232) completed a Sexual Health History Calendar (SHHC) assessing behaviors over the previous 12 months, risk self-appraisals, and future behavioral intentions. Youths’ narratives included negative self-appraisals (36%), named a risk-related critical incident (13%) or regret (9%), or expressed increased risk awareness (9%) and need for behavior change (18%). A minority were positive (28%) or reflected improvement (7%). All Phase 2 participants (n = 122) identified at least one specific risky behavior they intended to change. These data and the SHHC’s visual cues facilitated risk-reduction intervention tailored to the unique circumstances in which each youth’s risk taking occurred. For nurses and other providers in clinical settings, the SHHC can offer a critical link between assessment and intervention.