I have had to deal with saying no to a yf and the ensuing challenges but never with one who is as old as the one you describe. He is no longer even really a 'young adult' or whatever you want to call it.

I guess you can talk to him about how he is an adult and needs to take responsibility for his actions. Almost everyone has some kind of issues minor or major and you can't be successful in life if you let these issues become an excuse to not do what you need to do.

If he has not had a job for 18months then he needs to go out and try real hard to get one. Find something he can do with his depression. Maybe he can go back to school part-time if full-time was his problem.

It may hurt you but he needs you to lay down some limits. He is an adult and needs to act like one.

Godspell