Participants will engage with a variety of AI platforms that could be used to support language acquisition at different levels of proficiency, and to discuss some of the logistical, ethical and curricular challenges of these tools. As language teachers, we see an exciting potential for AI to offer our students authentic but scaffolded conversational experiences, and can imagine ways that teachers of other disciplines might incorporate these platforms into their lessons (ask Lady Macbeth about her motives, chat with Marie Curie about radiation). We are interested in exploring ways to train chatbots to work with content and concepts that are specific to the level and the material that we are teaching, while also considering how to account for the inherent biases in these systems. We will highlight a variety of emerging character-based AI conversation partners, and ask participants to consider the pros and cons of these resources in service of their curricular goals.