How Generous Should We Be?

Some days ago I was at the store getting myself a breakfast platter. One of the local homeless guys who I greet on occasion came over and asked me for a dollar. I generally don’t carry cash, and I told him this. He said that he didn’t care for the money, all that he wanted was an “egg and cheese.” He asked if I could get it for him. I did.

This leads to my question on how generous we should be? Every time I go to the store now, he hovers around me, and watches me. My concern is that I have created someone who will attempt to always gain from me because of my act of generosity.

We all work, we all have debt, and we all have families to feed. I don’t mind being generous on occasion, but this guy is always around here. I don’t want to be a jerk, but I certainly can’t afford to take up feeding another mouth on a regular basis.

I’ve been wondering if this is a normal internal dialogue? Generally, when asked for anything, I say no. This was the third time this guy has asked me for help, and I have always provided it. I’m wondering if that makes me a sucker, and in turn makes him dependent on me.

One guy I said no to, followed me after I said I didn’t have any change. He saw me make a purchase, and then had the nerve to say, “I saw you buy something, I saw you put the change in your pocket, I know you have change now, can I get it. Don’t say you don’t have any, cause I know you do!” I said, “No, and stop following me before we have a serious problem,” his aggressive and stalking manner pissed me off. I didn’t like that at all.

This other dude, he’s generally helpful to people out here, and he stands around the cabbies hanging out. I’ve seen him sweeping the sidewalk, guiding people to where the cabs are and so on. I figured, he’s trying a bit, so I would help him that one time. However, I don’t want to create a dependency, and I fear that’s where he is headed.

What are your thoughts?

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