The aim of this article is to investigate children’s playful shared movements on the preschool playground and to understand their doings when they perform apparently new and unexpected movements in these meetings. Video observations and field notes from two preschools constitute the empirical material, and we have analyzed three situations from the video observations to investigate the research question. The findings indicate that children in playful movement interactions use their habits to create moments that introduce something new and unexpected, what Daniel Stern (2007) conceptualizes as critical now moments. These now moments are opened up by imaginings, transformations, and excitement. In these moments, children can be creative and curious, leading to opportunities to experience growth in how they use their body and the place. Whether now moments led to creativity, growth and development, seemed to depend on the emotional attunement between the participants.