DS is 17 and generally a good kid from an outsider perspective - good grades, doesn't go out partying or get into trouble etc. He was always demanding, he came into the world that way I think. I remember saying when he wasn't even 2 that he was a real risk for becoming a spoilt brat. I won't go into it all here but we read book after book, I attended a parenting course and we sought every help we could to deal with constant demands. We did not give in or change our mind or undermine each other. It went from tantrums as a young child to repeatedly asking in an attempt to wear us down, to manipulation or lying. These days its nothing like that just a constant demand for more, more money, more lifts etc. We say no and we keep saying no and he will just ask again and get really angry about it. If its something we say yes to and he is happy I can guarantee he will ask for something else 5 minutes later, he always always pushes his luck. It has really damaged our relationship and we barely talk anymore because it involves him asking, me saying no or offering a compromise, him getting angry then maybe eventually agreeing to the compromise. When it comes to personal freedom I would say we have been quite liberal, more than some of our peers and to be fair he has always respected the limits we set, for example if he is allowed go out but needs to be home at a set time. He is very independent and doesn't ask us to manage his life, he also has a part time job now.
Part of the problem (if you want to call it a 'problem') is that we have a high income and I am home most of the time too. If he asks for something and I say its too expensive, he will accuse me of being tight. If he asks for a lift and I say get the bus he will say I'm doing nothing anyway only sitting around and I should be driving him. i should add he gets plenty pocket money and gets plently lifts too when appropriate. There were a couple of things recently that made me realise this is a very deep seated sense of entitlement. I overheard him talking with a friend about wanting something, he said 'I can be very persuasive, I always get what I want in the end'. He was genuinely gobsmacked when I told him he would have to buy his own car when he started working, he thought we would just buy him one. I could give 100 different examples.
Does anyone have this situation and what can I do about it, if anything. Do I just keep saying no and hope one day he improves? I feel I have really tried not to spoil him. Are some people just like this all their lives? DH feels he has a cousin who is like this too and nothing can change him. I feel I'll end up hating him and our relationship will always be difficult.