While the patient’s trust in the analyst is a much-examined subject, the analyst’s trust in the patient has been underexplored. Within a relational model that views affective vulnerability and risk by the analyst as inevitable and crucial to therapeutic action, the analyst’s ability to trust the patient is critical and inextricably linked to the patient’s sense of trusting the analyst. I describe and illustrate, through clinical vignettes, different aspects of trust that can impact the analytic process. Trust can be viewed as a prerequisite for analysis, as an analytic achievement, or both. The analyst may face the paradoxical challenge of attempting to work therapeutically with issues of trust when he or she does not feel trusting enough to do so.