A study of the relationship between playfulness and creativity was conducted with a sample of Japanese children who attended a preschool that emphasized whole-group orientation. Playfulness was assessed using The Child Behaviors Inventory, teacher interviews, and observations. Creativity was measured using The Creativity Thinking-Drawing Production Test (Jellen & Urban, 1986), The Drawing Test (Acharyulu & Yasodhara, 1984), teacher interviews, and observations. Although the statistical data analysis indicated no significant relationship between playfulness and creativity, the qualitative data analysis indicated that such a relationship may exist. However, conclusions must be qualified because analysis of the qualitative data revealed confounding factors in the concepts of playfulness and creativity. Some children who were rated by their teachers as non playful were described as internally playful and this internal playfulness was more evident in a one-to-one interaction and was manifest as joy, sense of humor, and active involvement. The internally playful child was described by the teachers as the child who possesses a lot of imagination inside but may not be able to express it externally in a group situation. Although the study focused on artistic creativity, the teachers in this study discussed a global view of creativity rather than artistic creativity. Thus, the results of qualitative data analysis appeared to contradict those of quantitative analysis. Further research on the relationship between playfulness and creativity is needed to understand such a relationship.