Two studies demonstrated that active efforts to appreciate a romantic partner’s unique point of view (imagine-other perspective-taking) lead individuals lower in self-esteem (LSEs) to feel less loved by their partner and less satisfied with their relationship as a result. These effects were evident regardless of whether individuals’ perspective-taking efforts involved reflecting specifically on a disagreement with their partner (Study 2) or not (Study 1). The studies thus identify a new path through which perspective-taking efforts can detract from relational well-being, one to which LSEs are uniquely vulnerable. Results from an open-ended thought-listing task administered in Study 2 confirmed that increased cognitive energy LSEs devoted to drawing (negative) metaperceptual inferences about their partner’s evaluation of them contributed to the negative effect of imagine-other perspective-taking on their perceived regard. No such effects were evident for individuals higher in self-esteem, and imagine-self perspective-taking instead exerted a general positive influence on individuals’ evaluations of their partner.