Facilitated by the cognitive impairment described in alcohol myopia theory (AMT), alcohol can be a catalyst of unplanned sexual activity, which can result in harmful emotional consequences that are particularly salient in women. We aimed to expand on previous research by examining how sociosexuality (permissiveness towards casual sex), gender, and alcohol influence the interpretation of a hypothetical alcohol-fueled sexual encounter. Participants (N = 107) were re-recruited from a 6-year longitudinal study in order to participate in a placebo-controlled alcohol challenge study. Beverage condition (alcohol; placebo), gender, and sociosexuality were used to predict negative affect and regret in reaction to a sexual encounter described in an eroticized experimental story. Negative affect and regret were measured both during the laboratory protocol and the following day. In a repeated measures analysis of variance model there was a significant time by beverage condition interaction such that the ratings of negative affect in reaction to a sexual scenario remained stable for those in the alcohol condition between the two assessments, while those in the placebo condition felt less negatively across time. When examining negative affect and regret during the laboratory protocol and the following day separately, women and those who are more conservative about uncommitted sex felt more negatively and had more regret after projecting themselves into the experimental story. Being intoxicated may contribute to labeling sexual behavior as atypical, attributing the behavior to an external source, and therefore labeling it as less desirable. In comparison, a sober sexual encounter may be attributed to a personal choice and thus, could be considered more aligned with personal values and may cause fewer negative feelings or less regret. Further, more permissive views about casual sex and male gender are protective against negative feelings about sex.