Pretend play in early years is considered key to the development of both children's and pre-service teachers' skills. Teachers' involvement in pretend play might be an effective tool for supporting children's play skills and self-confidence, communication, cooperation and decision-making. Drawing on qualitative interviews with pre-service and in-service teachers and on children's observations, this study identifies the importance of pre-service training on pretend play in childhood. This is shown by examining the pre-service teachers' skills development in organizing pretend-play activities with and for children. Eighty pre-service teachers, six in-service teachers and fifty children, aged between 2:6 and 4:0 years, participated in the study for three months, in Greece. Data was collected by video observations, dialogic interviews and field notes, all taken by the researcher, while descriptive statistical analysis was carried out. Results highlighted that pre-service teachers improved their own pretend play skills; overcame fears of exposure and were inspired by the children. According to in-teachers, children showed a greater willingness to participate in pretend-play games and became more confident in other activities. The paper concludes by reiterating the need to include active training with hands-on participation, and an emphasis on children's play at the syllabus of the university courses.