Stigma and negative stereotypes about unemployed people are likely to be distressing for individuals who experience unemployment. Nevertheless, empirical research on factors affecting unemployment stereotypes is surprisingly sparse. This article investigates an important aspect, namely, how personal and vicarious experiences with unemployment affect individuals’ generalized perceptions of unemployed people. The analysis is based on a unique data set consisting of panel survey data connected to rich, objective data regarding unemployment trajectories of both survey respondents and their relatives. It shows that both experiencing unemployment personally and having relatives who experience unemployment make individuals’ generalized perceptions of unemployed people significantly more positive. Moreover, subsequent analyses tentatively indicate that the effects fade when personal and vicarious unemployment experiences terminate.