Successfully managing interpersonal relationships requires both pursuing desirable bonds and forgoing those that could be costly. Balancing these goals might be more difficult for some than for others, especially for those with low self-esteem who are motivated to connect, yet stifled by their lack confidence in their abilities to attract desirable dating partners. So, when a potential date’s romantic interest is unambiguous, will they eagerly seize any opportunity to connect, or will the desirability of the person making the request influence their decision? In three laboratory experiments, single, female participants were randomly assigned to receive a romantic overture from an ostensible, single, male who was presented as a desirable or an undesirable dating partner. Independent of whether they accepted or rejected the target’s advances, lower, relative to higher, self-esteem individuals experienced more emotional and cognitive uncertainty and distress before and after making their decision. Desirability of the target moderated some of these effects, such that high self-esteem individuals appropriately distinguished between desirables and undesirables, whereas low self-esteem participants experienced distress at the thought of accepting or rejecting either target. Notably, the actual decisions participants made were unaffected by self-esteem, and driven instead by the extent to which the target was presented as possessing desirable social commodities. Results are discussed with reference to potential mechanisms driving self-esteem differences in balancing the pursuit of quality interpersonal bonds while avoiding costly relations.