Delimma...what would you do in my situation
He would be covered if you let him borrow the vehicle for free.

j/k no flames please!
I just saw Ferris Bueller for the hundredth time and couldn't help thinking that your "friend" might treat your E55 like the attendants at the car park treated Cameron's father's Ferrari.
Power does strange things to people.
You might offer to drive him around and/or double date. This might be a gracious out and preserve your friendship.
You're in high school, but even into my 20s with 20s friends, the weirdest sh*t would happen when I lent out my car. Once, my best friend who needed it for going to work and back (5 miles away) managed to put 200 miles on it while I was out of town - turns out she had lent it to her boyfriend and he must have really enjoyed driving it around ...
Another time I don't know what my baby had been thru, but I found a switchblade type knife wedged into the crevise of the backseat? Didn't even want to know about that one.
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