re: What do you do when grounding doesn't work?

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Arranged for our adult (ish) son to be home (who spent more time fishing than supervising)

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So you left Chet in charge?

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An entirely fair point. It was our 25th wedding anniversary, a two night stint planned months ago. Arranged for our adult (ish) son to be home (who spent more time fishing than supervising) and had a spouse unwilling to cancel. I have some responsibility in this, but also don't have complete control over the reigns.

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So you left the 21 year old son "in charge" of the 15 year old son and gave them the house for the weekend? I'm not saying they should have had a party, but you know your kids better than anyone. Was it likely?

As far as stealing the car goes, keep your keys in your bedroom. Put the spare in a safe. You shouldn't have to do this, but see below...

Teenagers are dumb. Water is wet. Most of the time you just have to save them from themselves!

I'm not supporting any of this behavior necessarily, but if he's an otherwise good kid - grades, sports, faith life, etc. - this really just sounds like pretty normal high school silliness.

This is where Daddy needs to have some man-to-man talks with his son. He is disrespecting you, his mom, and your family home/possessions. You have worked hard for these things, and he's not taking care of them.