A. There are many children who are shy, which doesn't mean they won't learn to be comfortable with all kinds of people. You have to start from where the child is, and build one success at a time.
First, help him to find activities that he likes and is successful with. The more times he can experience being good at something, the more confident he will become. He will also have the added advantage of having more to talk about. The more people involved, the better. Don't pressure him too hard to do things he's resisting, but don't make it too easy for him to opt out. Sometimes kids balk at doing something even when they know inside that they'll have fun.
Set up some social activities for him that will also turn out to be learning experiences. Start with something easy and work up from there. An example might be a movie "date" with a friend. They can have fun sharing a common experience, yet don't even have to talk.
Start with familiar structured activities with few people. As he gains confidence in being and interacting with people, then set up more challenging situations. Always set them at a level at which he will succeed, and quit while it is going well! The everyone will want to do it again.
Make sure these social occasions involve activities that he likes. If he likes computer games, invite some friends (one for the first time, then more) to come over and play them together. They will start talking about the games as they play.
If you visit adults, you can start the ball rolling by talking about his latest computer game. Let him correct you, or maybe supply some details of a particular level. You might cue the adults ahead of time as to things to ask him.
If he doesn't respond, don't force him and don't make excuses for him. It is his decision to talk or not. He will have to live with the consequences. It will be easier on him if you try to draw him into conversations. You might ask him a specific, open-ended question about the game. It might be something like: "How did Mario get lost in the Mansion in the first place?" Don't put him on the spot by asking a yes or no question and don't talk about difficult things or subjects he doesn't like.
Over time your son will feel more comfortable being around people and talking with them. He will slowly feel stronger when talking about things he doesn't know a lot about. If you can help make talking fun, then he'll do more of it. On the flip side, he'll talk less if it's hard or embarrassing.
Don't reinforce his vision of himself as "shy". If you call him that, he won't believe he can change. It could become an excuse used to get out of interacting with others. Build on his positive attributes by reminding him that he is kind, gentle, polite, and so on.
It may all take some time, but if you keep it all positive and affirming, he should get there.
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