A narrative inquiry project, Restorying Painful Histories foregrounds the effects of growing up in a world without self-representation in childhood. Specifically, this project attends to the aftereffects of misrepresentation and representational absence upon the imagination of queer educators. Addressing what Ebony Elizabeth Thomas describes as an “imagination gap” in adulthood, this project draws upon theories of critical literacy, queer studies, and affect studies as it invites queer educators to “restory” past experiences of queerphobia (i.e., a “painful history” of their choosing). Occurring over the course of one academic year, an inquiry community of nine queer educators gathered monthly at an LGBT center on a private University campus in the Northeast United States to explore the question: how might storytelling support queer educators address histories of queerphobia? During sessions, participants responded—affectively, orally, and in writing—to a shared Young Adult (YA) text featuring intersectionally diverse representations of queer adolescence. Following discussions of a weekly shared reading, participants then drew upon that work as a mentor text through which to rewrite a “painful history” of their choosing in a process called “restorying.” The restorying processes included six forms of narrative change, including rewriting identity, place, mode, perspective, metanarrative, and time. There are three primary findings from this project. First, queer individuals did indeed demonstrate an imagination gap, one that involves the active impulse to “destory” queer life. Isolating this gap revealed, however, the need to cultivate “affective reading” practices that guard against erasing queer history. Second, queer individuals are haunted by “genre ghosts,” by a realism that precludes happy endings and demands queer death. Through “critical speculative uptake,” however, queer people can brook the impulse to destory and bridge imagination gaps in adulthood. Finally, expanding criticality altogether, “reading orientations” are presented as a model for reconfiguring reader response theory to engage a wider range of forms of power. Specifically, “reparative description” reveals how power functions through the imaginative and affective aspects of queer educators’ “affective lives.” This dissertation concludes with a call for representational justice in pursuit of a queerer future.