Hi, I'll start by saying that I do actually love my Son but this will sound very negative because I want to know what to do about this issue.
My DS is now 9, I don't know if this is a realistic reason for it but he has been very indulged by his Father and his Father's family all of his life, he never learned there that crying won't get him anywhere, but he is only there EOW and half of the school holidays, so most influence is mine which makes me think I may be doing something to encourage this. When he is with me he takes disappointment on the chin mostly (leaves the tech when he's told time is up, comes out to walk the dog every day even when he can't be arssed) pretty much most inconvenient things he'll do even if he sulks a bit at first.
I've noticed recently that he has become known as a bit of a cryer in school, he said that someone called him a crybaby in school (one of the kids) and tbh I'm not surprised. He came out of school crying one day last week and said that the teacher had told him off for talking and that everyone in the line looked at him, so he cried, and then the teacher told him off for crying. He say's he doesn't like his teacher this year as she is very strict, to me she sounds pretty normal, just not flapping around the crying kid trying to appease.
It is a worry of mine because his Father is a very manipulative person and enjoys portraying a poor downtrodden victim and I don't want my Son to take the path of trying to look sad and hoping that everything is given to him too.
He had a friend here for a sleepover in the holidays and they were disagreeing over what to play, I overheard my Son saying to the other child "I'll cry" as if it was a threat or something, that pissed me off and I pulled him up on it, I've also seen my son sulk and pout trying to look sad when he's had friends over before, I feel like it's his default setting or something if someone is around to play for sympathy. My Mum was here yesterday and she wanted to walk into town so after fair warning DS had to put his lego aside and get ready to go out with us, I knew he wasn't happy about it but it's only one errand, I popped outside with the dog before we left, and when I got back in DS had tears in his eyes and my Mum was rubbing his back telling me that ds had a bad back from doing the lego on the floor. I told her that no ds always looks for problems if he doesn't want to do something and someone around could give him sympathy.
Today he has just been to rugby and the fucking face on him every time he was out of a game or did something wrong and had to be told, it was embarrassing, he cried twice and once had to be told by the coach that "everyone is learning" because of his sulky face!! It's like he takes everything very personally or something.
He does have good qualities by the way, I'm just zooming in on this flaw, which I think is getting worse as he gets older not better.