Put yourself in a beggars shoes if he has shoes!
You don't know this person ,never met them before.
You may or may not have the time to ask how they happened to be in the situation they are in.They probably wouldn't care to talk about anyway unless you promised to give them them something in return.
The person probably knows this anyway and simply asks you if you can spare some change for whatever they say they want it for..
If,they have a cigarette butt in their hand it's probably bumed off someone.If,they have a full lenth cigarette I'd ask where they got from.It's not likely that someone would give one to them ,but then I 'm not a smoker so I really don't know if anyone would or not.
By the way if the person doesn't have shoes then I assume they would be happy to get a pair as long as they fit.
The fact is all of us are victims of "social misfortune" at some time in our lives even wealthy people. They just happen to be dressed better than the average BUM!
Some of them even lived in mansions and are bank presidents,movie stars,etc.
I've heard some beggers in NewYork take in a fortune especially on "WallStreet"