When meeting people for the first time, we often strive to perceive others and express our own personalities accurately. Does this benefit social connection by promoting greater perceiver liking of targets, or might it instead hinder liking for some targets and in some contexts? In the present studies, we examined whether the links between accuracy and perceiver liking differ as a function of target self-esteem across two first impression contexts: a speed-dating context (N = 378, N = 4,797 dyads) and a platonic getting-acquainted context (exploratory sample: N = 557, N = 2,924 dyads; preregistered direct replication sample: N = 306, N = 1,683 dyads). In all samples and contexts, target self-esteem significantly moderated the association between accuracy and perceiver liking, such that accuracy was either positively related (platonic context) or unrelated (romantic context) to perceiver liking when targets were higher in self-esteem, yet accuracy was negatively related to perceiver liking when targets were lower in self-esteem, regardless of context. In sum, being seen accurately may have negative social implications for some targets and, especially, in higher stakes getting-acquainted contexts. (PsycInfo Database Record (c) 2024 APA, all rights reserved).