The aim of this study is to discuss and make clear how teachers need to interact with five-year-old children so that they can cultivate skills of communication through play with rules. We recorded episodes of children playing with rules, and examined teachers' better interaction to develop five-year-children's skills of communication from interaction between children and teachers. This study reveals the following four points are important when teachers interact with children. 1. Teachers' interaction which gives children opportunities to think what to do; 2. Teachers' interaction which lets children express their feelings with ease; 3. Teachers' interaction which observes conflicts between children's own feelings and others; 4. Teachers' interaction which makes children feel that they enjoy playing with their friends. In the future, we would like to make it clear how teachers' interactions should be so that five-year-old children can develop their skills of communication depending on the details of their play.