Transhumanists, like other elites in modernity, place great value on human creativity, and advances in human enhancement and AI form the basis of their propos- als for boosting it. However, there are problems with this perspective, due to the unique ways in which humans have evolved, procreated and socialized. I first describe how creativity is related to past evolution and developmental aspects in children, stressing pretend play and the ambivalent character of creativity. Then, I outline proposals for enhancing creativity, be it in embodied humans on the way to a superior species, in AI- related beings (virtual reality, robotics), or even in any degree of mixture in human- machine interaction. In the final section, I describe intrinsic limits to these proposals, such as the absence of a good understanding of human psychology by the proponents of enhancement; the lack of interest in the subjective side of creativity (for one’s own sake); delayed maturation and the ambivalence of pretend play in childhood; and the contrariness typical of new human generations. As for the enhancement of creativity, it is argued that creativity in its social context may be the victim of its own past success. On the other hand, an asymmetry between virtual beings and children is described— the latter can behave in a nasty way, it is part of their growth and creativity, whereas the former are not supposed to cause any harm to human beings. In sum, despite impressive progress in several scientific and technological interventions in creativity, philosophical questions emerge that place many constraints on transhumanist dreams of endless creativity.