Dreams can function in children’s books as a means to connect young characters and older figures in the story. In this article, Vanessa Joosen presents three methods to study intergenerational encounters in and through dreams in a selection of contemporary Dutch children’s books. She does this by means of a digital analysis of a corpus of 81 books to shows that the older the characters are, the less they are described as dreaming. Next, a close reading of intergenerational dreams lays bare, amongst others, the associations of dreaming with healing and death. Finally, a reader response study reveals that young children already understand some dream mechanisms and that older readers sometimes may draw on Freudian theory to interpret dreams, but that some also resist that.