Why are the parents ok with it? Seems like a given that the house would get trashed.
Have you contacted the home-owner parents to see what they have to say? It might go a long way toward making your DS feel like you're taking him seriously as a "grown up" teen if he sees you have a conversation with them about the house, the location, what they imagine will happen there, the safety plan, costs, etc.. You don't even have to consider for a moment saying yes, but it will both make your son feel heard and give you a chance to feel these people out and figure out what the hell they're thinking.
If you call, just do it from a position of information-gathering, not accusation, "Hi Mr. and Mrs. X, Larlo wants to go on the trip your son is planning this summer, and we are inclined to say 'no." Before we do, though, I wanted to talk to you about it and find out more about where they would be and what the island is like."
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