What do we learn by attending to what play and competition do? I am attempting to weave together multiple entangled registers of play and competition through recounting ethnographic snapshots of outdoor swimming along the Southeast coast of England. Approaching outdoor swimming with a playful disposition opens up the possibilities for radically new experiences. In turn, these experiences can become experiences to chase, moments to forget, or stories to retell amongst friends. Each moment of play in new waterscapes offers the opportunity to experiment and improvise in an ever changing world. It is through play and competition where the competitive swimming ethos is re-interpreted within recreational contexts, bringing new meaning to relatively stable notions of training, fitness, racing, and “lane etiquette.” However, this same ethos may also be shaped towards different ends, engendering change in the ways competition and play are reimagined in shifting waves. Through offering ethnographic examples a group of outdoor swimmers’ practices I argue that when approached playfully the changing conditions in this recreational practice offered possibilities for shifting the frame of activity, that is, by incorporating competition as a value into the mundane activity of swimming. The development of “good skills,” in this regard is crucial. I argue that approaching the practices of swimming with a playful disposition assists in attuning one’s skills and development within changing fields. The unpredictability and emergent forms found within changing fields (both the shapes and forms of water but also the forms of swimming activity) requires interpretation. And it is in this interpretation and interaction between swimmers, water, leisure, and competitive structures, that swimmers can demonstrate their skills and capacities to play well in an uncertain world.