He sounds very controlling. I second what SWOT said. I know you love your son, but he shouldn't treating your daughter in law like this. It is really over the top. She cannot go out with her girlfriends? Really?
But I don't think you should enable him to protect her.
I would not cook him any special meals. I would not buy with him in mind when you go grocery shopping. If he is not working, why is he asking if he can order out? Does he have your credit card or something?
Ugh, brings back memories of buying all his favorite frozen food crap, making special meals for him because h e was depressed and he was a fussy eater, ordering a sandwich for him because he wouldn't come out of his room to come out with us. I finally stopped doing this on the advice of my sister in law. My nephew was a real gift from God, but he is doing much better these days.
That's what I would do...make it not so comfortable for him.
Maybe he needs to be out of the house during the day. He can go to the public library and use their computer to look for jobs. We actually did this with our son. He did get a job. (Although that was not the end of his problems, but at least it's something on his resume). Gave him 5 $ for lunch. He was locked out till we came home.
It is so very hard to detach. I still struggle with it, in a different way, as my son hasn't lived with us for over two years, although if he had his way, he would still be here.
I remember your other son. He had a wife and kids, and addiction issues, as I recall. How is he doing?
I am so sorry, Oregami, that you are going through this (expletive) with another one of your offspring.