I Must Have "Sucker" Tattooed on My Forehead

I've been struggling with a theme this week, and it seems to be popping up on a daily basis - helping others less fortunate than myself. I know we are supposed to do this, but after my experiences, I can see why most people don't. I was walking to our apartment complex mailboxes on Saturday to get my mail, when I am stopped by one of the residents, an elderly African American gentleman - we'll call him Bob - with his dog. Bob informed me that the mailman was not done delivering our mail yet, but that he would wait because he is waiting for a grocery gift card which he needs because he has no food in the house. He also let me know that at least a neighbor had been kind enough to hook him up with a beer and a cigarrette. He went on to explain that once he gets his card, he would have to walk all the way down to Albertson's, then push the shopping cart all the way back (which is about 1/2 mile away). Well, like an idiot, I felt sorry for him and offered him a ride to the store. He gratefully and immediately accepted, and told me he'd let me know when the mail gets done. So I walk back to my apartment and begin knitting, and in a few minutes, he knocks on my door. I take him down to Albertson's and, when we get there, he asks me if he can leave the rest of his mail in my car. I put on my best "dumbfounded" face, since my intention was to drop him off at the store, then go home. He then asks me, "are you going to wait here for me or are you going to come in?". I mumble that I will come in with him. All throughout our shopping trip, he is mumbling about "now, I can't go over $70" and "I need this to last me for two or three weeks". I am silent and irritated throughout our shopping excursion. We finally get to the checkout counter and the clerk rings up his items, but it is soon apparent that all of the groceries will cost more than the $70 he has on his card, and he instructs the checker to stop when the total is close to $70. When she does, he still has quite a few groceries left on the stand, and I stand still and quiet as he assures himself that "I've done pretty good". The checker looks annoyed at the amount of "go-backs", and he gives a silent pause, but I remain quiet. I know that the expectation of his is that I will have a heart and help him out by buying the rest of his groceries, which I refuse to do. Finally, he asks the checker to ring the rest of the items, and that he will just pay for them with cash. We get the groceries out to my car, I drive him to his apartment, and set the groceries on his outside step for him to deal with, then leave. A little while later, I feel guilty for not helping out a little more, and bring him some of the fish I caught. All seems to be well - I don't hear from Bob on Sunday. Then Monday, I am stepping out the door, and he is there asking me for a ride to the closest military base to buy some things. Even if I didn't have a good excuse, I'd have refused. I am now past being irritated with him - and now irritated with myself. I felt no danger in offering this man help, but it's clear that no matter how much I help, he will need more. What I find even more exasperating is that he has rambled on and on about trying to afford groceries, but also has a dog and a smoking habit, both of which are expensive. I also don't understand why this man is living in one of the most expensive places to live if he's on a very fixed income. The other thing that complicates matters is that Bob is a disabled veteran - he served in the Vietnam War. I have very strong feelings about the treatment of our veterans, since my son's grandpa (on his dad's side) also served in Vietnam. He was in a submarine and became exposed to a harmful substance (I'm not sure which substance), and as a result, became sick with cancer. I saw first-hand how much assistance he needed, and I also heard some of his stories. I was there to witness how he would weep openly when he saw those advertisements about sending money to less fortunate children. Something happened to that man, but no one really cared that his life was forever changed. He ended up passing away from cancer when he was 47 years old - K barely got to know his grandpa. Like Bob explained to me, there's not a day that goes by that he doesn't think about the war and not a day goes by that he isn't affected by it in some way. But he's one of the lucky ones.

This is a big dilemma for me. I feel cold and heartless when I refuse someone help, especially if I have the means. However, when I do help someone of my own accord, I end up regretting it. Then I think about how that person lives and I start thinking that I'd probably smoke and drink if I had to deal with some of the things that people deal with. So, it's really not my place to judge. But I need to find my own way to help on my own terms, otherwise I will just end up feeling like a sucker and not help at all. I know that's not how it's supposed to be.