Education in virtual worlds has the potential, it seems, for engaging students in innovative ways and for enabling new discourses on a host of issues. Virtual locations like "Second Life," "Kaneva," or "World of Warcraft," among other multi-user virtual environments (MUVEs), also come with unique challenges for educators as they consider the affordances and risks involved in introducing new technologies into the classroom. Virtual worlds themselves require additional pedagogical and technological scaffolding if they are to function as fun and creative spaces for students. Further, the nuanced interactions of "real" classroom spaces are sometimes lost in representational virtual spaces. The authors' experiences both as students learning in "Second Life" and instructors teaching in virtual environments led them to invent a dialogue that reflects the complexities they have encountered. These two characters (Bored and Lost) were inspired from their own experiences as graduate students who were, indeed, bored and lost in virtuality. After each dialogue, the authors offer a response to how thinking about these students' positions might lead to a more critical pedagogical stance where virtual worlds are concerned. While many teachers are aware of the benefits of incorporating virtual worlds into their classroom practices, whether as part of specific assignments or as part of larger semester-long goals, they must also consider how they set up their students' entries into virtual worlds.