Wow. I can't imagine how he is going to pay loans if He is unemployed. I imagine he borrowed tons of money if he is still paying it 20 years later! He might need to see a therapist, there must be something going with him that he'd quit well paid job. Wow. It appears that unless he seeks help for himself (or you quit supporting him) nothing will change. I can't imagine how you two manage. You must make tons of money. We both hold well paid full time professional jobs yet we have not much money for extras.