Recognition of the costs of loneliness, in terms of public coffers and people’s health, is a relatively new phenomenon. That cities can be experienced as lonely places is nothing new. Responding to this, urban design focuses primarily on designing parks, housing, and plazas that bring people together in public space. However, these designs tend to encourage sociability amongst the already connected and do not address the social needs of lonely people who often feel daunted by the presence of others in public space. In this paper, I compare and contrast David Foster Wallace’s novels and Edward Hopper’s painting as different artistic treatments of loneliness, in order to argue for the memorializing of everyday urban experiences in public space capable of increasing public awareness regarding the profound harms of loneliness.