This study offers a set of reflections on the relationship between risk and pleasure in the field of HIV prevention and care, as it mediates new biomedical prevention/care technologies, particularly pre-exposure prophylaxis (PrEP), among men who have sex with men (MSM). We begin by investigating some studies about condomless sex between men, more specifically barebacking and PrEP use among young MSM. We base our analysis on the assumption that PrEP, as one of these new actants, has reconfigured the field of HIV prevention/care, especially in relation to the dimensions of risk and pleasure, with the potential to considerably reduce the chances of HIV infection while enabling maximum pleasure and a sense of greater safety and freedom. Despite this progress, we also problematize some of the ambivalences, tensions, and moral conflicts that still exist in the field of prevention, especially the potential for condomless sex. Finally, taking a praxiographic perspective on health care and foregrounding the situated practices of human and non-human actors/actants in interaction, we consider HIV/AIDS prevention as a more fluid, non-linear, erratic phenomenon that involves multiple types of knowledge, feelings, and participations, and is open to different kinds of experimentation. Besides a “logic of choice”, we hold that health care is a permeable, continuous process that is enacted in situated practices and may produce different effects in response to a heterogeneous network of interactions.