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Human judgments of similarity and difference are sometimes asymmetrical, with the former being more sensitive than the latter to relational overlap, but the theoretical basis for this asymmetry remains unclear. We test an explanation based on the type of information used to make these judgments (relations versus features) and the comparison process itself (similarity versus difference). We propose that asymmetries arise from two aspects of cognitive complexity that impact judgments of similarity and difference: processing relations between entities is more cognitively demanding than processing features of individual entities, and comparisons assessing difference are more cognitively complex than those assessing similarity. In Experiment 1 we tested this hypothesis for both verbal comparisons between word pairs, and visual comparisons between sets of geometric shapes. Participants were asked to select one of two options that was either more similar to or more different from a standard. On unambiguous trials, one option was unambiguously more similar to the standard; on ambiguous trials, one option was more featurally similar to the standard, whereas the other was more relationally similar. Given the higher cognitive complexity of processing relations and of assessing difference, we predicted that detecting relational difference would be particularly demanding. We found that participants (1) had more difficulty detecting relational difference than they did relational similarity on unambiguous trials, and (2) tended to emphasize relational information more when judging similarity than when judging difference on ambiguous trials. The latter finding was replicated using more complex story stimuli (Experiment 2). We showed that this pattern can be captured by a computational model of comparison that weights relational information more heavily for similarity than for difference judgments.