I gave one guy my old pocket-umbrella because it was raining and he (obviously) didn't have one (or he'd have been using it). New condition, I never used umbrellas because I never stood out in the rain more than a minute or two.
A woman who I hadn't seen before had a nice message on her sign, said something like "Please smile and have a blessed day" or some other similar sentiment. I was first in line at the red light so I gave her a chit-chat, asked her if she had a cat for a pet - I would've given her one of the cans I'd just bought. She said she had a dog. After another minute of chatting while waiting for the light, I grabbed a handful of change from my car's change compartment and handed it to her. She had horrible teeth. I'd never hire someone like that as a "public face" for my company, because her front teeth were black and pitted, one was missing. Her skin was clear, her hands were clean (because even homeless people know how to use a rest room).
Homeless people have trouble getting a job because most jobs require that they have a permanent address. When you fill out an INS form, you need proof of residence. Without that, you can't get a legal job in this country.
No permanent residence = no proof of residence = no legal job - even if you had good teeth.
I don't normally ever give money. That one woman though was very personable, obviously intelligent, polite and articulate? My guess is that she was bulimic at some point in her life (long-term bulimia causes the enamel to strip off your teeth and then they turn grey, and then they start to rot). I really hope some dentist sees her some day and volunteers to give her a new smile.
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