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

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No it's not. He made a commitment to the girl he invited, and her parents have likely invested money to get her there. It's a pretty big deal to have your date back out the Monday before the dance. This is showing him that he made a promise to her, and he needs to keep it.

He can do pictures, dinner, dance, then get his butt home. His date can go to the after party (that's all they care about anyway). He will feel stupid. She will still have fun.

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Oh horse shite! No way should that kid get to go to Homecoming! As others have stated his date's expenses, etc. should not factor into the equation. She could probably go with some friends or possibly even find another date.

I would hope that if the girl's parents are decent they would rather their daughter not attend the dance with a 15-yr old degenerate that obviously has no respect for his parents, rules, or anything else.