In this single-case retrospective study, we examine the phenomenon of difficult experiences in schooling and literacy as described by Diana, age 25. Drawing on convergent theories of affect, new materialism, and critical dis/ability studies, we explore educational trajectories and complexities of entangled identities. Four open-ended interviews, a series of conversations, were conducted with Diana and analyzed through a rhizomatic lens. Our analysis illustrates Diana's participation histories and literacy trajectories (re)presenting dis/continuities of past, present, and future time, which bring to life emotional collisions, ruptures, and possibilities. As difficult experiences compel us to witness and to bear testimony, we address potential social and human consequences of labels and categories and argue that a new materialist approach to literacy research and critical dis/ability studies can powerfully frame research that calls out injustice and cultivates hope.