AI-powered personas and roleplaying technologies offer transformative potential for enhancing empathy and communication training in military contexts. These innovations create realistic, adaptive environments for simulating various interpersonal scenarios and developing crucial soft skills like cross-cultural communication and conflict de-escalation. Key benefits include scalability, customization, safe learning environments, and data-driven improvement. The technology can be integrated into existing DoD training frameworks, enhancing personnel readiness for challenging conversations and complex interactions. By adopting AI-driven roleplaying, the DoD can pioneer new approaches to empathy-driven communication training, potentially reshaping military preparedness for an interconnected world. The presentation explores current research, emerging technologies, and potential applications in this field.