We wanted to examine whether narcissism affects the level of discrepancy between expectations for a vacation and the vacationer's actual experience. Using a pre–post panel design, we explored the association between narcissism and the confirmation of expectations for a vacation (the difference between the expectations of participants prior to a vacation and how they actually experience the vacation). Our sample consisted of 219 community-based vacationers (107 men and 112 women) from urban areas of Israel. The average age of the participants was 33.91years (SD=8.47). Participants completed measures at the beginning and end of a three-night vacation in a resort city in southern Israel (Eilat). In addition to a measure of pathological narcissism, the participants completed measures of their affective expectations (Time 1) and subjective experiences (Time 2). The link between pathological narcissism and positive affective expectations was moderated by gender such that pathological narcissistic personality features were associated with larger discrepancies between affective expectations and subjective experiences among men. Men with high levels of the vulnerable form of pathological narcissism reported being less satisfied with their vacation experiences than other individuals. These results suggest that narcissistic personality features and gender play roles in the anticipation of potentially pleasurable events, as well as how those events are actually experienced.