re: A good buddy called me asking for money yesterday. Update 6/12

Your friend has an obvious problem of maintaining a lifestyle he cannot afford. That is a big problem that takes big life changes to correct and a real humbling of his priorities in life. His toys may have not be paid for either. He may have notes on them and be upside down on them. Selling them may still leave him in debt to the lender. He could surrender the toys to the lender if this is the case and work out some sort of payback of the balance. It happens. As his friend, I would consider the amount he wants to "borrow". If it is a few hundred then I would not loan it to him. I would gift it to him, "bless" him with the money. Then there is no expectation of repayment and you remain a good friend to him. If it's thousands then I would explain that you cannot afford to do that and you would be happy to help him sort out some other choices he could make. That might be your opportunity to help him understand what's really necessary going forard. I mean if he has all of these toys, he must be insuring them too, right? All of that, with maintenance and upkeep gets really expensive really fast. If he is looking to you as another form of an ATM then you're not really his friend. You're just a source of cash. You'll also know this if blessing him once turns into another request for money and he hasn't made any changes to his lifestyle. I know this is long but this is not an easy situation if he is really your friend. Best of luck but you may still lose a friend no matter how kind you are.