Today, social skills are essential to success both on the job and in life. However, practice environments for social skills are typically out of reach for most people. How can we make social skill training more available, accessible, and inviting? Existing mechanisms for practice and feedback largely rely on expert supervision, making training difficult to scale especially given the shortage of trained professionals. In this talk, I share two of our recent works on social skill training using LLMs. The first one explores how to empower therapists in learning therapy skills with LLM-empowered feedback and the second one looks at training people with conflict resolution skills via simulated practices. We conclude by discussing risks, concerns and mitigation strategies related to LLMs-based simulation for social skill training.