The unique nature of the COVID-19 pandemic prevented many typical graduate assistantships from occurring due to school-building closures, virtual classes, and stay-at-home orders. As such, the authors address the increase of 'shadowing' graduate assistantships at a large land-grant institution. To uphold the governmental stay-at-home regulations per COVID-19, shadowing provided first-year students with exposure and access to more experienced graduate student instructors ('the shadowed') who taught undergraduate and graduate coursework. In this autoethnographic study, the authors investigate the following questions: (1) In what ways did our experiences align with Mentoring Enactment Theory and Social Exchange Theory? (2) How might we better align our conception of shadowing to both theories? The article finishes with modifications to the theories in light of the shadowing experiences.