My two-and-a-half-year-old son is quite shy. When I have another child over or we go to their house, it takes him about two hours to warm up enough to play with that child, even if we have had playdates with that child several times in the past. Of course, after 2 hours, it is then time for us to go home! I am not shy myself, so I don’t know how to deal with this. I don’t push him, but I wish I could help him be more comfortable.
Mother of one, age two-and-a-half
Repeated playdates with the same children are a good place to start. I might have repeated play with the same child several days in a row and at the same house. If the parents can manage you might also, and I don’t suggest this often, stretch the playdates to three hours. If your child is warming up at the two hour mark, you want him to have some success. Now, this plan requires you have a good friend with a child who is willing to participate in this process. You might also take a few pictures of them when your child is warmed up and playing and then show and talk about that fun time often with your child. It is reminding him of the fun that was had.
You might also plan more playdates at places that he particularly enjoys. If he really like a particular playground, plan some of your outings there. Children may be able to bond over the shared activities.
Also, realize he is only two-and-a-half years old. Many two year olds are still in parallel play where they play more beside someone than with them. This is more the case for boys as well. So the interactive play may still just be developing. Give it some time and continue with the play opportunities.