The Middle Arc II: Brave Conversations (AKA Difficult Dialogues) describes ways to support interpersonal and group interactions during the middle part of the semester (about weeks 4 to 13), particularly through brave conversations. We consider “What is happening with students, class dynamics, and faculty” at this stage as interpersonal dynamics become more conflictual and tense. We examine the psychological processes behind these dynamics, applying psychological theories related to positionality, socialization and identity development. We offer strategies to effectively negotiate these dynamics and maintain student learning through engaging three emotional and relational processes: fostering perspective taking and empathy; promoting community and relational learning; cultivating reflexivity and exploration of positionality. At this point in the course, interpersonal strategies focus on facilitating brave conversation through developing empathy and perspective-taking skills, focusing on the process and goals of difficult dialogues as informed by psychological theory, strengthening a sense of community through in-depth exploration of intersectionality, and managing conflict when things aren’t going well. We also provide strategies for faculty self-care during this time, focusing particularly on ways to manage one’s own responses to the intensity of the relational interactions. The chapter concludes with Reflection Questions for faculty to explore how the material may apply to readers’ particular styles and contexts, inviting faculty to consider their emotional and personal responses, and make active choices about application. Additional resources related to the specific chapter content are also included.