Social media platforms such as Facebook and Twitter serve millions of people who populate digital space with autobiographical avatars and simulacra. Digital selves are curated, edited, and maintained in a perpetual process of digitizing life experience in order to produce an imagined life. The emergence of social media poetics—and, specifically, what I term digital realism—demonstrates the use of the confessional mode in social media. Digital realism gives name to a process of literary production that obscures the lines between life and writing. In this essay, I explore how digital realism operates in the work of multimedia artist Steve Roggenbuck (b. 1987), which draws out and capitalizes on the contradictions of self-fashioning through affective modes of sincerity and failure, in order to explore the limits of popular accessibility that social media platforms and poetics purport to offer.