I think his resentment has built up over the years from me wanting to see more of him and to be appreciated more and him feeling guilty and getting mad at me because he feels guilty.
In my opinion he struggled with feeling like he had to defend his mother at every opportunity and justify her actions.
Example: She and I discussed getting him a car when he turned 17, I say I will share the cost. My son and I look at a few just to get any idea what he wants but don't get anywhere near actually buying one.
We are still talking about it when I find out she went ahead and bought him one with no discussion with me. And a crappy one at that. subcompact Chevy Aveo. Small and dangerous. Then she wants me to pay 1/2.
I say you gave it to him, you pay for it.
He defends her.
A few years later when he is tired of the Avo, he and I shop together for another car. I keep his mom informed on what we are looking at and let her know we intend to buy one, a Honda Accord. He uses half the money from the Aveo and I pay half. That was this summer !!
The next payment for school is due on Nov 3rd.
I don't know what to say to him I'm afraid that anything I say will just make him more mad.
But I feel like a sucker for just sending him thousands of dollars.
I'm also reinforcing the idea that he can play victim and get away with it.