My child was always very shy. She is an only child and very intelligent, but I sometimes think her goal in life is to go unnoticed. We have really tried to help her, by putting her in situations that would help her learn how to participate in groups. We taught her about social expectations, just like we taught her everything else.
We told her that if she does not respond to other people, they may think she is not very friendly.
Is there any way he could attend school all 5 days? Also consider putting him in a private pre kindergarten class. This way he will have an entire year to prepare for "real" school fall 2010. Could he take swimming lessons, art classes? This way he is meeting other children in different situations. We also used to do as many group things with our neighborhood, so she would have some friends when we went to other events. We also tried to do a lot of volunteer things since she was young. This was a great way for her to be exposed to a variety of people.
We all want to protect our children from being frightened, embarrassed or feeling alone. But these are the things, that as parents we must teach our children or they will never learn to be independent.
Does he know how to greet people? When you introduce him to other adults do you have him shake hands and say hello? If not teach him to do this. Do not refer to him as shy. This gives him an out. Just let him know that people like to know who he is and the way to honor that, is for him to respond. Practice introducing him to people he already know. Also have him practice with stuffed animals. Have him introduce you and his father to his stuffed animals.
When he meets other children, he should respond with hello. Every time. Practice at home.
Also when you go to a restaurant. Teach him to order what he would like. Teach him to look people in the eyes. These are rules of our society and just like rules of behavior, he will feel like if he knows rules, he can follow them. Practice at home at dinner. Let him be the waiter and have him serve you. Always use please and thank you. Have him place the order to you. Remind him some restaurants are loud, so he needs to speak up. Maybe offer him dessert of his choice if he will order his main meal in a restaurant. If you go to a fast food place have him place the order.
He may never be really social and out going.. Our daughter does ok, but I wish she were more confident in public. It did help that as she got older, her grades and accomplishments, forced her to be recognized and she realized she was successful, but I worried when she went so far away for college. She finished her freshman year with great success and told us her goal is to be "House President" Her junior year! Never, has she ever done anything like that before. We are thrilled, but not making a big deal out of it in front of her.