For educators looking to include literature with lesbian, gay, bisexual, transgender, and queer or questioning (LGBTQ) characters in their libraries and classrooms, it is sometimes difficult to determine which books contain authentic and accurate representations and avoid stereotypes and problematic tropes. Drawing upon J.K. Rowling's paratextual "outting" of Professor Dumbledore in Harry Potter and Dav Pilkey's in-text disclosure that a leading character in his Captain Underpants series is gay, this article examines ongoing professional (and primarily pedagogical) conversations about sexuality in youth literature, describing political and literary considerations for teachers and all readers evaluating children's books depicting gay male characters.