Educators and learners alike are feeling the impacts of stressors and uncertainties in and beyond higher education. Because we come to our learning spaces as whole people, and do not shed our identities, goals, values, and experiences at the classroom door, these stressors may manifest in the classroom as difficult or disruptive conversations. In this session, we will reflect on our own experiences with difficult conversations, explore the ways that difficult conversations arise in the classroom, and identify proactive and reactive strategies for facilitating challenging, respectful, and caring conversations.