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Modern communication technology has greatly increased the number of options we can choose among in a variety of evolutionarily important domains, from housing to food to mates. But is this greater choice beneficial? To find out, we ran two experimental studies to examine the effects of increasing option set-size on anticipated and experienced choice perceptions in the modern context of online mate choice. While participants expected greater enjoyment, increased satisfaction, and less regret when choosing from larger (versus smaller) sets of prospective partners (at least up to a point; Study 1), participants presented with a supposedly ideal number of options experienced no improvement in affect and showed more memory confusions regarding their choice than did those participants presented with fewer options (Study 2). Participants correctly anticipated that greater choice would yield increasing costs, but they overestimated the point at which this would occur. We offer an evolutionary-cognitive framework within which to understand this misperception, discuss factors that may make it difficult for decision-makers to correct for it, and suggest ways in which dating websites could be designed to help users choose from large option sets.