This chapter focuses on the roots of play and playfulness in children's early experience of relationships. It seeks to argue that the current debate about the loss of safe outdoor play spaces, and the dangers of over-reliance on digital entertainments, sometimes neglecting the fact that play and playfulness are developmental achievements, and that there are huge variations in children's capacity to make use of the opportunities they have. In reality, play activities can be taught, but playfulness is a state of mind, and as such, cannot be taught or learned in the ordinary sense of those words. It takes time and skill to foster playfulness in a parent-child interaction. Although environmental factors play a significant part in the promotion or otherwise of 'healthy' play opportunities, playfulness is a state of mind, and one which is established within a relationship.