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This qualitative study aimed to determine how men and gender diverse individuals who have sex with men describe their perceived risk of HIV and what factors influence this risk assessment. We conducted in-depth, virtual interviews with 18 HIV-negative individuals from Philadelphia, eligible for or taking PrEP. The interviews assessed the participants' understanding of their HIV risk, using thematic analysis to deductively code and extract themes. Three themes emerged: (1) participants expressed both deliberative and affective risk perception before and after sexual encounters; (2) participants linked HIV knowledge to risk perception and stigma; (3) participants connected intrinsic and extrinsic factors to risk perception differently. Participants endorsed low overall risk perception, while also describing moments of high affective risk perception after sexual encounters in which they were not able to implement their preferred prevention strategies. Future research should explore helping individuals transform affective risk perception into empowerment around sexual health.