He's a dependent person. It's a pre-alcoholic or pre-addiction phase. He wants you to be responsible for him and for his emotions and bad feelings. The only cure is make him stand on his own two feet - the longer he is allowed to manipulate you using guilt, the sicker he is going to get. A kid like that only gets better when he runs out of enablers. Kick him to the curb, let dad pick him up, dad will probably kick him to the curb next. Help him out when he is own his own as little as possible - humanitarian help only - the kid is starving, buy him some groceries. Soon he will be faced with two choices, either start playing ball with you or joining the service. To tell you the truth, nothing would be better for him than Uncle Sam. The shape the army is in, they will probably take a kid without a diploma.