Mental health practitioners, assessing children for possible psychiatric conditions, need to probe sensitive matters. We examine practitioners’ use of questions which try to clarify a given issue by offering alternative descriptions of how things are: one bland, and the other clearly undesirable in some way. The undesirable states of affairs can be described in serious terms (e.g. the child wanting to kill themselves) or, while still undesirable, in less serious ones (e.g. the child feeling temporarily upset). We find that if an undesirable state of affairs is described in seriously negative terms, it tends to be put as the first item in the pair of alternatives. We argue that this version of the familiar ‘optimistic questioning’ practice ensures that were the negative case to be chosen, it would be in spite of it being the more interactionally difficult answer to give. That makes the answer diagnostically more reliable. We discuss the pros and cons use of this practice in the environment of triage.