Might as well prepare them for credit card debt now

I can not tell you the number of times a child has come up to the counter with four or five things and $20. Usually it goes something like this: I scan their items, typically a necklace for $7.99, a stuffed animal for $13.95, a sucker for $2 and some other candy for $2.75. I tell them their total. Their response, "Oh, I don't have enough [sad look]." Child, I really do not care. The child in question then will remove the cheapest thing and ask, "How much is it now?" Still too much, child, still too much. Once they decide that they can, in fact, live without the candy, they're down to the necklace and stuffed animal which are still about $2 too much for them even before tax is added. This is when the chaperone nobly steps in and offers to give them the extra money. To which the child replies, "I'll pay you back tomorrow." I'm willing to bet that the chaperone never sees that money again.

I understand if a kid miscalculates tax and is short a few cents, by all means, give them that small amount. But when you have to give a child or even multiple children $5 because they can't afford a stuffed animal that will probably either be thrown out or go to Salvation Army in a few years, it's unfair to you and the children. I understand wanting to make them happy, but you are already teaching them to want things they can not afford. It will only get worse from here so stop it now before they have a real shopping problem and live in a cardboard box with nothing except that necklace and stuffed animal. If only they had bought that candy, then the would have something to eat.