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Using virtual environments (VE), we examine—for the first time—how individuals’ traits predict “first date,” in-the-moment conversational choices. We look at how attachment anxiety, avoidance, and Behavioral Inhibition System (BIS) predict virtual conversational choices (ie, to dismiss, deny, or reciprocate in virtual conversations during a virtual date). We tested this possibility through socially optimized learning in virtual environments (SOLVE-IT), a web-based, interactive 3D video game intervention designed for young men who have sex with men (YMSM) to reduce risky sexual behaviors. Data analyzed were drawn from 358 HIV-negative, self-identified MSM aged from 18 to 24, who were part of the SOLVE-IT intervention. Using ordinary least squares regression, we found that both BIS and attachment styles affect in-the-moment conversational responses and that attachment moderates the effects of BIS on those responses. The implications of these findings are discussed.