This article explores the dynamics of inter-generational conversations between queer and trans youth and queer and trans adults through an analysis of a routine segment on the reality show, RuPaul's Drag Race. At the end of each season, the drag queen contestants are asked to give a piece of advice to photos of their younger selves and, by proxy, the young people who may be watching the show from home. This article positions this segment as a pedagogical moment where the queens are forced into the role of teacher. However, like the categories of child and youth, RuPaul's request of the queens is not as innocent as it appears. In turning to address children directly, the queens must reckon with cis-heteronormative expectations of how adults can speak to children, about what topics can be discussed, and the tones such conversation must take. To explore these issues, the article examines this segment alongside scholarship about drag and ballroom cultures to place the show within larger contexts of queer and trans kinship structures. Then, turning to queer and trans studies in education and queer and trans childhood and youth studies, the essay examines the factors impacting how and when queer and trans youth and adults are allowed to be in conversation with youth, if at all.