How can you tell?
Because 99% of the people that randomly walk up to me at a gas station or rest area are looking for money.
Last time a guy at a gas station asked me for money, he was a pretty young kid who looked like he'd been living in a dumpster for a while. I had bought a big pile of granola bars to horde at work for snacks, so I gave him a chunk of those instead of money. At least I know he had food, instead of spending it on booze or something else possibly.
My dad and my life experiences have taught me this is a good way to go. Buy a meal, fill a gas tank or can but I don't give cash. More than once I have seen a meal offered to someone who claimed to be hungry only to watch them clam up & walk away. I told a lady that said she needed gas to pull up and I'd use my card to put $20 in her tank and she walked off, out of the parking lot. Before I was done I saw some dude get into the Honda that she said was hers and drive off, it wasn't even her car - I'm guessing she was on foot hustling. These experiences are what have jaded me, I always hold & open doors, everybody gets my respect until they prove they don't deserve it and in the scenario described I probably would've taken some time to help the OP's wife. But I can't fault people for being cynical either. Heck, Walmarts have been sued by customers because they accused the guy jumping their car of screwing up electronics. Helping nearly always makes you vulnerable in some way and there are people looking to take advantage of the vulnerable.
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