Title: Empathy based Affective Portrait Painter DiPaola, Yalcin Can an AI system using a set of state of the art AI modules, act like a portrait painter who first meets a sitter, chats with them to understand who they are and then using their experiential sense of that person create a portrait that both archives a fine art personalized portrait of both the outer resemblance but also the inner ( resemblance of) mood and gestalt of that sitter. We will combine the two main areas of our research lab, Cognitive based empathy in AI conversational agents and our cognitive-based creativity AI painterly system to have: 1) Viewers 1 by 1, talk with our AI empathetic fully 3D character agent system ( our painter) 2) Based on analysis and mood of that conversation (empathy modeling) create a fine art portrait 3) Display that Portrait on the large projected wall with our portraits, newest first