While the title of John Updike’s short-story collection, Trust Me (1987), and the theme of betrayed trust of the first story (“Trust Me”) offer a thematic coherence to the collection, it would be restrictive to read the stories through the simple thematic filter of betrayed trust leading to weakened human attachments. Trust is given a wider articulation in the collection, that of a mode of connection for human beings to their world, their lives, and to others. The loss of trust for the protagonists in the stories, “The City” and “The Wallet,” is undergone as just such a loss of connection, engendering in both cases an existential disquiet. The article explores the nature of these existential crises, situating them within Updike’s wider deployment of the motif of the fall in his collection. The article goes on to consider the manner in which the existential theme of these two stories is informed by Updike’s own recurring existential unease, a reflection justified by the avowedly autobiographical dimension of his short fiction.