The image of the empty chair as a metaphor for loss is well known in works for adults but is less frequently used in children’s picture books. This may not be surprising when we consider the weight of meaning the empty chair conveys in one simple, stark image. The empty chair functions beyond the words used in the books and allows the child to make meaning from the image. It can allow the child to ask questions not posed by any text alongside the image and also provides a vehicle for the child to access the “big questions” about loss. Children’s picture books can use this level of profound communication—taking the child to a level of understanding beyond that which adults might normally expect of the very young—tending as we do to shield them from difficult subjects. The images allow us to consider not only loss but offers ideas of hope and continuity. This chapter looks at two powerful examples of the empty chair in picture books.