In two preregistered studies, we find that initiators of unrequited romantic advances fail to appreciate the difficult position their targets occupy, both in terms of how uncomfortable it is for targets to reject an advance and how targets’ behavior is affected, professionally and otherwise, because of this discomfort. We find the same pattern of results in a survey of science, technology, engineering, and mathematics (STEM) graduate students (N = 942) who recalled actual instances of unwanted or unrequited romantic pursuit (Study 1) and in an experiment in which participants (N = 385) were randomly assigned to the roles of “target” or “suitor” when reading a vignette involving an unwanted romantic advance made by a coworker (Study 2). Notably, women in our Study 1 sample of STEM graduate students were more than twice as likely to report having been in the position of target as men; thus, our findings have potential implications for the retention of women in STEM.