Counterfactual reasoning (CFR)—mentally representing what the world would be like now if things had been different in the past—is an important aspect of human cognition and the focus of research in areas such as philosophy, social psychology, and clinical psychology. More recently, it has also gained broad interest in cognitive developmental psychology, mainly focusing on the question of how this kind of reasoning can be characterized. Studies have been inconsistent in identifying when children can use CFR. In this article, we present theoretical positions that may account for this inconsistency and evaluate them in the light of research on counterfactual emotions.