You are a very generous person and to a fault.
A bit of advice from someone who has worked with the homeless.
Never introduce yourself, never give them your name, never shake hands with them.This is all for your personal protection.
In regard to giving them something like food, money, etc... DONT
There are Social Services of the local area homeless shelters, food pantries, TANF - Temporary Assistance for Needy Families, Food Stamps and Emergency foodstamps, vouchers from Salvation Army for clothing, householdgoods, etc.
Make a list for yourself with contact numbers if needed but NEVER EVER engage because the example you are citing has access to all this and more.
Its a grift
For example, in my time spent there was a homeless woman who begged on the street while having benefits and sleeping in a shelter.
She was eventually placed in a apartment with full benefits including $$’s from state sources.
One day a friend of mine and I were driving to Burger King and at the entrance to the parking lot she set up shop with a folding chair and sign saying she needed “ help - anything is appreciated”.
We looked at each other and busted out laughing.
“..set up shop with a folding chair”
There were two well-abled guys that would take turns in the wheelchair with their “disabled need help” signs.
My wife and I have monthly donations to various places. The local groups help homeless people and are Christian based, and require sobriety, drug free, etc. to use their services (housing, education, job training and having actual jobs).
I have been known to give a bottle of cold water on a hot day on occasion.