Scholars have called for ethnographers to reveal the emotional and controversial aspects of fieldwork. Through analysis of our fieldwork with teens in the United States and Japan, this article documents how we, two adult researchers, attempted to address adultism--a pervasive system of oppression that deems young people inferior. We discuss three types of encounters which we believe reflect how adultism operated in our fieldwork and the challenges related to de-stabilising it. The encounters revealed specific patterns and manifestations of adultism including 1) how adults regulated young people's identities, 2) our assumptions about what rapport and reciprocity with youth meant, and 3) the dilemmas of whether or not to deploy adult power to intervene in youth dynamics we found to be troublesome. This article suggests that adult researchers reflexively examine and document challenging and unsettling moments with youth in fieldwork in order to interrupt and unlearn adultist behaviours and beliefs.