Drawing on social comparison and equity theories, we investigated the role that perceived similarity of a comparison target plays in how resentful people feel about their relative financial status. In Study 1, participants tended to choose a comparison target who was better off, and they selected a target they perceived to be more similar than dissimilar along dimensions that surrounded their financial outcomes. In Study 1, perceived relative disadvantage was positively associated with resentment regardless of the perceived similarity of the comparison target. The results of Studies 2 to 5b clarified these findings by showing that being both similar and dissimilar to a target can cause resentment depending on the context. Using hypothetical and real social comparisons, we found that people are more dissatisfied with their financial outcomes when their comparative targets have the same background qualifications (i.e., are similar) but are financially better off (Studies 2, 3b, 4, and 5b). However, we also found that when the comparative financial contexts were similar (i.e., equal affluence), participants were more dissatisfied when their target for comparison had lower qualifications (i.e., was dissimilar; Studies 2, 3a, 4, and 5a). In all cases, perceptions of unfairness mediated the effects of social comparison on financial dissatisfaction. Taken together, these studies address some of the ambiguities around what it means to be similar to a target in the context of social comparisons of affluence, and they underscore the importance of perceived unfairness in the link between social comparison and resentment with one’s financial status.