This paper focuses on the sexual behavior of Puerto Rican men involved in primary relationships with other men. The data are drawn from two separate and consecutive studies. The results of the first study show that those men who have both lovers and one-night stands (n = 67) are more likely to have unprotected anal sex (receptive and insertive) with their lovers regardless of HIV status. The qualitative data collected in the first study as well as the in-depth interviews of mixed status couples in the second study document that participants with adequate information, will power, and skills to protect themselves engage in risk behavior in the absence of external barriers to condom use. The wish for sexual pleasure and intimacy and the trust and love for the partner often overpower concerns about HIV transmission among coupled men. Cultural issues such as machismo and gender roles also have an impact. The need to devise prevention mechanisms that will not interfere with physical pleasure or intimacy is underscored.