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HIV is most prevalent among men who have sex with men (MSM), and although most MSM use condoms consistently during casual sex, some take risks. To better understand the psychology of those risky decisions, we examined neural correlates of playing a virtual sexual ‘hook up’ game in an functional magnetic resonance imaging scanner in MSM who had, in the past 90 days, been sexually risky (N = 76) or safe (N = 31). We found that during potentially risky sexual choices, previously risky MSM had more right insula activity than previously safe MSM. Real-life sexual risk was related to trait positive and negative urgency. Insula activity that differentiated risky and safe MSM was related to trait positive and negative urgency. Future work should further examine if, and to what extent, insula activation during safe sex negotiation drives MSM’s rash risky sexual decision-making.