Because of the COVID-19 pandemic, we are all now living in a world of mass panic, confusion, and isolation that inflicts experiences of mental illness on those not typically considered mentally ill. When, where, and how does identifying “mental illness” come to trap certain people under the stigmatizing identity, while others are able to avoid the problematic medical classification but not the lived experience? As a writer mitigating a long-term struggle between my lived experiences with depression and anxiety, and the outside categorization and medical classification of these “mental illnesses”, I realize the current public sentiment has never been more welcoming of my personal musings on these tensions. I have centered an autoethnographic approach that reflects on mental health experiences and critiques of biomedical ontologies through a reading of My Brilliant Friend (and the associated quadrilogy). By attending to socially relevant story arcs involving mental health, I use the symbol of book character Lila’s “blurred boundaries” to both identify and rethink mental health categorizations and lived experiences that previously differentiated subsets of people prior to COVID-19. My reflection ultimately seeks to address the ways that these once dissimilar groups have converged psychologically through disruptions of time during the current health pandemic.