Self-reported HIV risk perception and behaviors are used in a variety of settings for diverse purposes, such as HIV prevention program planning and screening. Careful consideration of how youth in high HIV prevalence areas interpret these kinds of questions warrants attention. The Cognitive Interviewing Project (CIP) conducted cognitive interviews on common risk survey items with 30 cis-female and 20 MSM youth (18 to 24), who had recent sex with a male partner, in Cape Town and Vulindlela, South Africa. Results identified a number of potential issues including (1) confusing text; (2) mismatches of terms with local usage; (3) confusion with items requiring self-tailoring; (4) presentation concerns limiting selection of full range of answers; and (5) challenges reporting on information dependent on partner (eg., HIV risk, HIV status of partner). Self-report Items used to identify those at elevated risk for HIV should be evaluated with local populations to optimize shared understanding.