Is your son shy in other ways too? We have an article on our website about helping children when they are feeling shy that might interest you.
"If your child acts shy, he needs you to lovingly accept and validate him, just the way he is, while at the same time warmly encouraging him, indicating that things are actually safer than he can tell...Before going into a situation that you think your child may find frightening, try using our method of Special Time. Children clearly thrive on moments when we are just with them. Take ten or fifteen minutes before you get ready to go and shine your undivided attention onto your child, and do whatever it is that he enjoys doing with you at the moment. Play pillow fight. Drop lightweight balls down the stairs together. Allow some messy water play. Put your child in charge of the interaction and follow him, letting him be in control of the relationship for a time. Radiate enthusiasm for his ideas and desires. This will help to bolster his connection to you and help him store up a little extra confidence for the challenge ahead."
There are lots of fun ways you can help children with shyness. I hope you find some that you and your son will enjoy trying.
Hand in Hand Program Director