We proposed in the "Veil of Darkness" hypothesis that dark personalities (narcissists, Machiavellians, psychopaths) profit from conditions of less illumination where they can better manipulate others. As an initial test of this hypothesis in the domain of mating, we predicted that male dark personalities should be more successful in their courtship during dark/cloudy rather than bright/sunny weather. In a large naturalistic field-study, 59 men romantically advanced 1395 women on the street, while they were unobtrusively followed by confederate observers. We thus obtained ratings from men, women, and observers on women's reactions to men's advances. Machiavellians, but not narcissists and psychopaths, elicited more positive reactions from women during cloudy weather. This effect was mediated by Machiavellian men's assuredness. We discuss different mechanisms that may constitute the observed Veil of Darkness effect for Machiavellianism. (C) 2014 Elsevier Ltd. All rights reserved.