TL,
You're right that it's easier to detach when difficult child behavior is blatant. I've experienced the same.
Canteen: You placed $20 in his account, but instead of thanking you for it, your son demanded more. Classic. In his world, he actually feels entitled to it. But you don't have to participate in his world, which is out of touch with reality. And any guilt or pity you may feel for him plays into his manipulation to get what he wants.
Phone Calls: I agree with MWM that you may benefit from setting some boundaries related to phone calls. Teach him how to treat you with respect.
Girlfriend: While your difficult child can make his own choices, you definitely should not feel guilty with disengaging from helping him connect with his girlfriend. The relationship is not helping him. Whether or not the pregnancy is real, and it may not be, your son can use it to try to manipulate you into giving him what he wants. My difficult child did the same thing, and it turned out there was no pregnancy.
Drug Court: You mentioned about going to court to support your difficult child. I suspect going would be harder on you than appreciated by him. Do take care of yourself and consider how this is affecting you.
Ultimately, your difficult child needs to get more concerned about his drug problem than the jail canteen, phone calls, and girlfriend. It sounds like he isn't there yet, and I know that is very hard. The sooner he becomes extremely uncomfortable with his situation, the more likely he will be to seek and successfully participate in treatment to heal himself. You are on the right path, and you are very strong. You are recognizing behaviors and learning to not enable. Whether or not your difficult child ever recovers, you can continue to take extra good care of yourself and lead a joyful life. We all understand and are here for you. I will keep you in my prayers.
