Through a combination of social change and legislative initiatives, the workplace has been transformed from a rigidly stereotypical environment (i.e., with males and females occupying distinct roles) to an arena that offers equality and opportunity for all. Regrettably, however, individuals who perform traditionally counter-stereotypical roles (e.g., male nurses, female pilots) continue to experience significant disadvantage and dissatisfaction. Why then is this this case? The authors explore the possibility that this may be due, at least in part, to unexpected events that trigger implicit negative associations. The results of two experiments support this hypothesis. Individuals depicted in counter-stereotypical roles activated negative evaluative responses, an effect that was most pronounced for male targets. The theoretical and practical implications of these findings are considered.