This article explores and analyzes the help-seeking and risk-taking behavior of Black urban street youth in Washington, DC, USA and Cape Town, South Africa. The target population of 100 youths came from the streets of Washington, DC and Cape Town, South Africa. Structured face-to-face interviews and direct observation of informal and formal settings where youths congregated were used to gather data. Major findings indicate that the majority received high levels of support from families and friends. In terms of formal systems, social and mental health services are viewed as much less accessible or useful. Youths were knowledgeable about HIV/AIDS but did not translate this into safer sexual practices. Implications for health and social policy are outlined.