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When you say "strict suburb" do you mean residential area? In those cases they WILL get you for 3 miles over unlike an interstate which they usually don't mess with you until 5 miles over.
Personally I think it would be "odd" to offer the guy money but I'd make a comment like cutting back for a while and maybe make him dinner and pay for videos etc. for a while instead of going out on costly dates. That would "help" him and yet he would keep his dignity.
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