There is increasing concern about declining mental health amongst children in the UK and the USA. Evolutionary and anthropological theorists have begun to build a theory linking this situation to decreasing opportunities to engage in free play. This paper will explore typical contexts for children in these nations, concluding that a range of recently emerging environments have decreased opportunities for collaborative peer free play and ‘discovery’ activities for the current generation. We will draw the theoretical analysis from a broad area of research encompassing psychology, anthropology, education, sociology, marketing, and philosophy to offer a new blend of practical and theoretical perspectives that may shed further light upon this topic.