One of the most taxing issues in the prevention of heterosexual transmission of HIV in Puerto Rico is culture itself. Researchers point to the need to change cultural norms related to gender and sexuality to reduce HIV transmission: traditional gender roles that dictate the need for unprotected sex as a measure of relationship trust, understanding monogamy as an HIV prevention strategy, and the role of religion in discouraging condom use as a prevention effort. Although these issues are complex enough when addressing individuals, they become even more multifaceted when addressing couples that feel safe from HIV by having steady partners. However, when one partner in the dyad is HIV positive, implications for prevention are even more daunting. The purpose of this chapter is to contribute to a better understanding of HIV risk and protection in serodiscordant couples in Puerto Rico, by employing exploratory qualitative interviews with 20 such dyads.