South Africa is often cited as being a society in transition. Travelling from apartheid to utopia, the metaphor implies, we are transforming in the in-between. For Winnicott, transitional spaces reside in between internal and external reality, offering an intermediate area in which to play. It could be said that, in contrast, apartheid structures impeded such transitional spaces; they defined where and where not to play, who could play with whom and what was serious and thereby not available for creativity. By analyzing narratives written by South Africans remembering apartheid as part of the Apartheid Archives Project (the narratives themselves potentially, but not always, representing a transitional space), I first explore how space is remembered and inscribed, including how physical spaces, such as beaches or restaurants, are carved out by the act of remembering. Second the narratives, written now about then, offer possibilities for exploring transitions between the past and the present and implications for playing in the present and the future.