The author proposed fourteen difficult moments that happened in the initial sessions of child play therapy. They were: ”when a child does not come to playroom (separation anxiety or anxiety of strange situation)”, ”when a child does not talk or play”, ”when a child criticized the equipments or toys of playroom”, ”when does the therapist show the rules of playroom to a child”, ”can therapist play with children?”, ”when a child will take toys home”, ”when a child does not want to end the session”, ”when a child wants to bring another child to the playroom”, ”does clean up the playroom should be a rule of playroom?”, ”when a child test a therapist in the playroom”, ”when a child comes too late”, ”when a child brings food to the playroom”, and ”Issues of recording in the playroom”. Based on his clinical and supervision experiences, the author explained his conceptualization ideas and suggested some techniques to solve these difficult moments.