Common strategies employed in preventing STI/AIDS transmission among young adults in America include abstinence, monogamy and safer sex. These strategies require a high level of vigilance and responsibility and, according to inner city participants in Project PHRESH.comm, neither option is always desirable, available, or rational in the context of their lived experiences. This article reports findings from Project PHRESH.comm, a mixed-method, ethnographic study incorporating data from focus group discussions, semi-structured interviews, coital diaries, systematic cultural assessments and a structured survey designed to explore concepts of risk and decision making about condom use among at risk African American and Puerto Rican young adults aged 18-25 years in Hartford, CT. We found that many young adults from our study population rely on a strategy of using clinic-sponsored STI/AIDS screening when wanting to discontinue condom use with a partner. While our data suggest that screening is a common strategy used by many couples to transition to having sex without a condom, the data also show that most youth do not maintain monogamy even in long-term, serious relationships. Thus, sharing test results may provide a false sense of security in the sexual culture of inner city, minority youth.