Postdevelopmental pedagogies challenge us to forego a focus on developmental ticklists and milestones and instead engage with the messy riches of experience as it unfolds in the moment (Sakr & Osgood, 2019). As part of this project, this chapter reconceptualizes early childhood art as an “entanglement” (Barad, 2007): a “complex and lively manifold of entangled and changing practices and possibilities” (p. 388), in which myriad, perhaps endless, elements are constantly “intra-acting with and mutually constituting one another” (p. 389). What happens if we think about moments in early childhood art not as bounded in time and space (as suggested by the developmental paradigm), but instead as wormholes through which we travel to multiple “reconfigurings of what is and what is possible” (p. 389)? To explore this further, the chapter shares an observation of young children playing with chalk in the family home. Exploring the observation as an example of entanglement, the chapter challenges us to consider three important aspects of children’s art making: (1) reconsidering the traditional parameters of observational tools and processes; (2) following the affect flows in the observation as a means for unsettling typical ways of making sense of children’s art making; and (3) reintegrating care and responsiveness into how we think about and do observations of children’s art making.