Job candidates often encounter illegal questions about their personal life during interviews. Through five multi-method studies, we delve into the reasons behind interviewers asking such questions and the motivations driving candidates to answer them. Our findings illuminate a stark contrast in perceived motivations between interviewers and interviewees for why illegal questions are asked: while interviewers deem their queries as well-intentioned, job candidates, especially women, interpret them as veiled attempts at discrimination. We also identify two factors—insinuation anxiety and mistrust—that arise when candidates face such questions. Insinuation anxiety pressures candidates to comply with interviewers’ requests to disclose personal information that they would rather not reveal to avoid insinuating that the interviewer may be biased for asking such questions. Mistrust reduces the job candidates’ desire for the job. Our studies highlight how the presence of illegal demographic questions can alienate women and marginalized groups from the workforce.