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Originally Posted by LivingAlmostLarge
So I’m curious what most people would do in this situation?
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I would not let another person borrow my car unless it was some dire emergency.
Since that obviously isn't how you feel, what I would do doesn't really matter. The question is what should you do. What were the ground rules when you first started allowing him to use the car? You said that he is on the insurance policy. Is he paying his share of the premiums? If not,why? If you didn't charge him anything at the outset because you thought it would just be a rare occurrence that he used the car, then you all need to sit down and discuss the fact that he's using the car a lot more than you anticipated and he needs to start paying for his share of usage, gas, maintenance, etc. if he wants to continue using it.