Here's my take on it. I dated someone just like your son last year for eight weeks. This guy was 33. I refused to give him any money at all, although he started hitting me up almost immediately when we started seeing each other. He always had a good story (temporarily short on cash, waiting on a check, waiting on some work to come through, blah blah blah, quack quack quack..) but I couldn't see giving him money ever.
So of course, his good ole mom was the last resort. It wasn't that he was using (as far as i know, he wasn't at the time). But her giving him money was what enabled him to keep from getting a job. And because he never was forced to get a job so he could live comfortably, he had lots of time on his hands. And lowered his self-esteem. No man can feel good about himself if he isn't working, IMO. The boredom and low self-esteem led to a nothing-to-lose attitude that eventually led back to drugs and crime. A bad relapse. He's back out there. I'm not saying it's his mom's fault, Lord knows we don't cause this sh!t, but who knows? Maybe if she'd stayed out of it, he'd have found a job, or at least hit bottom faster.
I used to sit next to him while he conned her on the phone "Please Mom, I don't want to lose my place at the halfway-house by not paying my weekly rent...then I'll end up stealing again..." I used to curse her for falling for it, and also felt very sad for her. He'd never let me talk to her or meet her, because he knew I'd tell her the truth. She didn't ever get my phone number, but after we broke up, his mom wrote me a letter asking me about him and what I thought was going on. I was too afraid to answer it, because he was already stalking me by then, but I wished I could have told her the truth. So I'm telling you instead. Stop sending money, dear. No good will come of it.
Love,
KJ