Ones I can remember:
We stole some tools and need to get out of town. wtf (What did I look like, the godfather)?
We came to town to go to church. Can you give us a couple bucks worth of gas to get back home? Sympathetic, but it was a weekday at noon.
We came from Town A to find work in Town B. Can you help us out so we can get (see above)? Persistent. Females. Red Alert!
We ran out of gas and are bumming our way to the coast to help a friend. Gave the two young men a ride to the nearest station (dumb), but that's it.
I'm in the service and need to get back to the base tonight. Again, sympathetic, but how does someone drive halfway across the state w/o money? Hmmm...
After giving $ to a sign holder once or twice, I learned my best response was a firm "no". Keeps me from making either the right or wrong decision! LOL
The worst one was maybe 25 years ago my dad picked a guy up who said he had sick kids at the house and needed money to get them meds. My dad picked him and drove him to the nearest pharmacy. Guy about blew a gasket when my dad offered to pay for whatever over the counter meds would help. Guy yelled and screamed at my dad and then walked off.
My dad told me the story and then mentioned "you know the real sad thing is is he probably does have sick kids but still would spend any money I gave him on booze over helping his kids".