I don't think I could ever ask a stranger for money. It would be too hard.
I never give money to homeless people. I'll give them food, water, or cigarettes. There are so many tweekers and heroin addicts in Phoenix. I agree with their right to do the drugs, but I don't agree with their decision to do them. And you can tell the difference pretty easy here. Who is legit and who is just a druggy. But I still will give the druggies food if I can. The legit people are usually crazy, though, and don't usually want help. They just want attention.
I hate people trying to force my emotions to feel. I hated it in church when they would play soft uplifting music when the pastor prayed, and I hate it when panhandlers give me puppy dog eyes. It's bullshit! I'll feel what I feel, and don't try to force my heart. I some times want to punch then in the face when they come up and beg like little pathetic people. Then they turn on you when you ignore them.
I know that there are people in other countries, and times in history, that need to beg to live. I have even done charity work in Mexico before. Those people where fucken poor. Living 6+ people in a 10' x 10' cement room. Hoping that when the harvest season is up, they'll be able to find work in the next town (migrant farming help). Where one very basic medical check up was a months wages. Now those people needed help.