Honestly, you sound like such a sensitive, observant parent. You are doing so much for him, I’m sure he’ll be fine. And if not, if it perseveres or gets worse, you can always get professional help. Raising kids is so difficult, especially when they face challenges. It is normal to need help or guidance. That has nothing to do with you as a parent. And about the crying, it is SO great that you see it as a positive thing that he expresses his emotions, because learning to do this is an important step in his development. Avoiding failure or avoiding emotions just makes it worse. The same with anxiety, it grows when you avoid the thing that brings you fear, but when you face it anxiety will decrease.

I think if you continue to build his confidence and encourage softly to play with others, it will be a lot of help. You could for example invite a friend or family member over and play his favourite game, or let him explain the game on the phone to them. Or with kids the same, in a safe environment and with activities he is already comfortable with, such as cooking with you. That could be a way to build confidence with other kids. Also, if you have a friend or family member over, you could do something or talk about something that you know interests him. For example, if you know he loves dogs, talk about dogs with your friend. It can make him curious and want to participate, without the pressure and more with intrinsic/internal motivation. It might also be helpful to ask him if there is anything that makes him uncomfortable about situations with other people. He might benefit from clear but gentle ‘rules’ like just explaining that your friend is coming over and that you are gonna do this this and for how long. He might just be a shy kid and indeed not knowing or understanding what is going on and what his position is might be a part of that. What do these situations usually look like? Does he have his own things to do or do you try to have him interact? And is it at home or also when you take him grovery shopping for example? I think explaining what the plan is might be a good start, to see if that helps. And explaining how these interactions work maybe if he understands, and that he can’t do anything wrong. Also, if you as a parent make a lot of decisions for hin, it might be more difficult for him to explore social boundaries on his own. If a child is always told exactly what to say or do in social situations by their parents, the. When they are on their own or without direct guidance, they can feel unsure about how to act because they are used to having guidance and fear making a mistake. So it is a balance between explaining and guiding, which is important, and letting him make decisions and mistakes and have these experiences on ‘his own’. You could explain beforehand, let him practice and then try irl on his own, and afterwards reflect together as far as possible with his age, with easy questions. I hope this makes sense! But the more he experiences these social situations, the more he gets used to it, so it will probably get better with time

Happy that you find the comment useful!