The problems psychopathic individuals impose on society and in their interpersonal relationships can be held in stark contrast to reports of their appeal and sexual success in some of those relationships. In the current paper, we seek to contextualize this enigma by focusing on the interpersonal dynamics of psychopathic individuals in romantic encounters. We first formulate a plausible evolutionary function, the sexual exploitation hypothesis, that proposes psychopathy exhibits “special design” features for subverting female mate choice, facilitating the induction of favorable (...) impressions and desire in prospective intimate relationships. We then test the hypothesis in two studies with university samples. Study 1 had young men assessed on psychopathy, social intelligence, and sociosexuality engage in a filmed dating interaction. Study 2 had young women view a subsample of the videos, rate them on desirability, and leave voice messages. Results show psychopathy was related to sociosexuality, specific factors of social intelligence, and generating higher desirability ratings from women after controlling for men’s physical attractiveness. Analyses involving comparisons of two men showed women’s ratings increased in favor of the more psychopathic man. Women’s voice pitch also changed, but only in response to different facets of psychopathy. The results provide preliminary support for the sexual exploitation hypothesis and suggest that more dynamic assessment of putative desirability in psychopathy may be required to capture its plausible special design features in prospective dating encounters. (shrink)