This article introduces a forum of response articles to the edited volume Masculinities in Text and Teaching. The forum features two scholars of English in a transatlantic conversation and then a response by the editor of the volume. The forum develops, from the edited collection, the theme of pedagogical uncertainty in studies of masculinity and the ways those conversations can be used to help students develop their own humanistic ethics in the classroom. Employing two styles of doing work on teaching from the perspective of textual scholars, the author of one article reads her own experience and classroom moments to build an argument about the high stakes of doing work around gender for students and the profession. The other author reads from both classroom experience and from a text she teaches to open up new pedagogical possibilities. These techniques are echoed in the collected volume. A key argument throughout is that classroom struggles around texts and identities — which often provoke feelings of vulnerability and uncertainty for both teachers and students — can be deployed in conversations that enable students to learn about both the humanities subject and themselves.