You can actually learn a lot about children’s friendships by observing their play with peers. If you notice that your child prefers to play with younger children, as opposed to children his own age, perhaps playing with the younger children allows your son to take on a leadership role he has not been able to assume with his same-age peers at school. He might feel more confident playing with younger children, and that’s okay. Try not to force him to play with children he feels uncomfortable around. Instead, talk to your child about what makes him special and why he is a good friend. Your role as a parent is to help him build confidence and learn what it means to be a good friend.