Recognizing one’s own playfulness is important for early childhood education (ECE) teachers, who are responsible for organizing and implementing child-initiated pedagogy in kindergarten. Playfulness research has focused on children’s play and playfulness in workplaces, but playfulness as a part of ECE teachers’ pedagogical orientation and adaptive expertise is rarely studied. Using multiple playfulness measurements, first- and third-year pre-service ECE teachers’ (n = 208) self-reported playfulness was examined. Correlation coefficients and t-tests were performed to examine the connections between the facets of playfulness, adaptiveness and inquisitiveness. The results of the study show that, although there were no statistically significant differences among the groups, they had different orientations towards playfulness. As their education proceeds, pre-service teachers should be able to integrate theoretical knowledge and practical knowledge to focus on children’s needs and the quality of interaction with and among children and to take steps towards adaptive expertise. Additional research is needed to explore how teachers and pre-service teachers can learn playfulness as a part of their pedagogical expertise. The results are implementable for designing, developing and evaluating ECE teacher education.