Pretend play leads to real-life learning. By imitating a firefighter using a horse, a doctor checking a patient's ear, or a construction worker building a skyscraper, children learn about community roles and services and feel proud and satisfied. When they pretend, children create pictures in their minds of past experiences and use their imaginations to think of new scenarios. These thoughts and images let children think about situations and objects that are not right in front of them and events that have not yet happened. Pretending elements are essential to cognitive, emotional, social, language, physical, and creative development. Through constructive play, children learn by making objects. Constructive play also helps cognitive, emotional, social, physical, creative development. Constructive play is a continuous problem-solving, process and constructive play provides a window into children's thinking (Forman, 2006). The main research questions posed in this study are as follows: (1) What are the pretending elements that appeared in constructive play? (2) What are the pretending elements that appeared in pretend play? and (3) What are the teacher's roles to enhance the pretending elements in constructive play and pretend play? The participants for this study were ninety-eight 5-year-old children (49 boys and 49 girls) attending childcare center and kindergarten located in A and S city in South Korea. One play session lasted for 30-40 minutes. Researchers observed pretending elements in pretend play were more specific and diverse than in constructive play. The constructive play also had symbolic and pretending elements. In constructive play, however, the progress patterns of constructive play were classified into three types. First, children do only constructive play. Second, children construct through blocks or clay, and then they pretend play using their creations. Third, children do constructive play and pretend to play almost at the same time (Park & Han, 2011). Lists of suggested material to facilitate both constructive and pretend play are provided. One very important observation to come from this study is that teachers need to provide plenty of time for elements of both pretend and constructive play elements to develop. Teacher roles in the enhancement of both pretending and constructive elements of play are discussed.