Parent-infant observation is an established aspect of preparation for psychoanalytic training or for enriching clinical skills. Despite the vast literature on this subject, there remains a paucity on the process of searching for a family to agree to being observed. This paper explores one post-graduate student's experience of this task as well as a seminar leader's reflections on working with this student and other groups of students at this stage. It is argued that each observer's search for a family to observe can provide rich material for reflection and represent a valuable learning experience for the individual.