This dissertation focuses on some of the philosophical puzzles that are associated with the experience of engaging in fictions. Some of these puzzles are longstanding in the philosophical tradition, viz., the paradox of fiction, the paradox of tragedy, and the phenomenon of imaginative resistance. Another has received surprisingly little philosophical attention: the puzzle of why we engage with fictions at all. I argue against what I will call the Simple Story of fictional engagement. Previous discussions have (to greater or lesser degrees) described engaging in fictions as a matter of entertaining the events described at a fictional world. In the Simple Story, the content of the fiction is decisively determinative of our motivations to en...