Researchers are increasingly interested in how clinicians should screen for suicide ideation in care settings and the merits of doing so. A common finding is that screening does no harm, and may do good, insofar as once the subject of suicide is broached clinicians can conduct a suicide risk assessment to determine the course of safe care. To date, little has been published about just how clinicians should ask “the ask” about suicidal ideation. The aim of this article is to suggest that the difficulty clinicians seem to have in initiating a verbal probe for suicidal ideation has less to do with patient characteristics than it does with clinician anticipatory anxiety about learning that a patient is positive for suicidal ideation. Face-negotiation theory and politeness theory are offered as possible explanations for why a simple direct question is so difficult to ask. Future research directions are suggested and an absence of data from public health gatekeeper training is offered as argument for clinicians to be more direct in their probes for suicidal ideation.