A transitional object is the selection and binding to an object that reminds the child of the mother and helps deal with separation anxiety in situations where the child is separated from the mother. In reality, many children are observed to have transitional objects and no problems occur. In this case report, the transitional object became pathological. An only child, the boy was 3.5 years and wished to wear the pyjamas chosen as transitional object in all areas of life. According to anamnesis from the family, there was no socio-economic problem experienced. Additionally, the child's developmental curves were normal and there was no physiological health problem. The child experienced problems in home and school life and this situation negatively affected the mother's home and professional life, so the case was dealt with. The study applied a strategy developed based on a behavioral approach combined with an object relation approach. At the end of the four-week program completed with the parents and child's teacher together, the problem was solved and follow-up one month later identified that this had not changed.