The author recounts their worst job interview experience, where they felt emotionally drained and vulnerable after being asked invasive questions about their personal life, including their hardest day and biggest life challenges. The interview was with a mental health startup, which the author found ironic given the sensitive nature of the questions. The author argues that while cultural fit is important, it should not come at the expense of making candidates feel uncomfortable or judged. The author suggests that companies should reconsider their approach to evaluating cultural fit.