The book examines the role of idealization in the process of intersubjective understanding and social interaction. I further Karl-Otto Apel’s conception of the dialectic of the real and ideal communication community, and examine our ability to generate counterfactual, “as-if” spaces from psychological, neurocognitive, and philosophical viewpoints. Rejecting the assumption of internal connection between acts and meaning, I argue that internal models can be accessed and assessed by means of embodied self-reflection, to further self-understanding and self-regulation, on the one hand, and intersubjective understanding and mutual coordination of action in the world, on the other. On this basis, I propose that ideals configure individual societies of mind that ideals us to map the social world and provide the necessary means of bootstrapping in the process of social learning and development. They are the missing link between facts and norms.