Helping the Correct Way
Margaret has given her son a bunch of money, but his mess still isn't cleaned up.
Dave's ANSWER: If I were in your shoes, I'd sit down and say that this is a bit of an awkward conversation for you, but you are in a position to help them financially and clean up some of the mess. But you want to make sure of a couple of things. The first is that you are actually helping them instead of making a bigger mess. If they are interested in you helping them pay off some of their debt, they need to think about that and think about if they are all right with you knowing their situation because that will be your only requirement.
You don't require that they pay it back. It will be a gift. But you don't want to become an enabler and be giving a drunk a drink, so you want them to show you where they are and that they are heading the right way. You don't want to be a control freak, and if they are in that situation, you'd like to help.
If they want to stay where they are and tell you to mind your own business, you can do that as well. You’ll still be their mom and you’ll still love them–you just won’t give them money. If you have given them money and want to do more, the only way I would do it is to know more about the situation. Again, not to be controlling, but to make sure you're actually helping instead of enabling them to continue bad behavior. You don't want to participate in causing them to not suffer the consequences of crazy. That helps them win and turn the corner.