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Is it good to give money to homeless people?

As you have found, they're not really after survival items.

How can you possibly know that? Did you conduct a scientific study? If so, where did you publish your results?

Or, wait. This is yet another example of you forming strong conclusions from anecdotal evidence, isn't it?
 
I give money to the local food bank.
That is a bad idea. When has a food bank ever stopped asking for money? You give and give and they keep asking. It is a bank for crying outloud. That food should be paying interest!

They are as bad as Public Radio. ;)
 
I guess you and I have different philosophies. When I give money it’s a favor asked and a favor given. I don’t think it’s unreasonable of me to want to see the money spent wisely.

It's not unreasonable to want that. It is however unreasonable to dictate what spending it 'wisely' means. It's not, after all, as if you're in any inherently better position to make that determination than a random other person; regardless of whether that person is homeless or not. Plus, it's wasting everybody's time: is it worth the hassle to make sure the bum spends the money you give him in a fashion you find appropriate? It's just a couple of bucks, if you're going to part with it, part with. Don't waste both your own time and the bum's by following him around or personally controlling how the money is spent by buying his food for him instead of having him do it himself. Besides, it runs the risks of making him feel really bad about himself. I know that if I were in that situation, I'd rather not have people treat me like I can't be trusted not to help myself. Sure, help me out... but leave at least some of my dignity intact while you're doing it please.


Be honest, if some bum approached you on the street asking for money so he can buy a car to go to job interviews with, you wouldn't give him money, would you?
Are you claiming to be psychic? How can you deduce what I would or would not do?

Because humans aren't that hard to figure out, and almost nobody would actually give money in that case; it defies their expectations. People see a bum and they immediately have a particular impression in their minds. When one asks them for money, they expect that either he's genuinely in immediate need and needs food; or that he's just scamming them to buy drugs or some such. If the bum tells them he needs money to buy a car; the image of him being in need gets demolished, and people will automatically revert to the alternative impression. It would take a lot of convincing on the part of the bum to override this type thinking, and a certain kind of receptive personality. You may or may not be the receptive kind, but chances are you're not the special kind of person who would give the guy money without the hefty convincing part if he falls outside of the normal pattern of expectation to such an extent. The only people who would are people who are incredible gullible... and psychics. And I'm pretty sure psychics don't exist.



Why do you think I give money to people in the first place?
:confused2:

The same reason anyone does: to make you feel good about yourself. If that isn't the real goal, why would we even be having this conversation?



I started this thread for advice, not to beat up or disparage homeless people. They are in an unfortunate situation.

It seems like you're struggling with on the one hand being upset by a particular negative perception you've developed about the way your help is used in a way not to your liking, and on the other hand the guilt that then follows from not helping people directly anymore. Like you want someone here to make it easy for you by breaking through the conflict and giving you a solution to follow. Now I could do that. I could make it easy and just give you the 'advice' you want instead of the debate you're resenting right now. But I'd be doing you a disservice by doing so. It's too easy; and doesn't resolve the actual conflict: which is that you're going to have to decide whether to either see about changing your perceptions, or find some way to live with the guilt.
 
Hello Dystopian,
Ok, I read what you wrote and decided to give it some thought and review the thread. I think I see where you are coming from, and you seem like a reasonable person.
You have given me some things to think about; both myself and my attitude, thank you. That was actually what I was looking for. I truly bear you no ill will. Truly.

I find writing to be difficult, and it’s hard for me to convey my ideas sometimes.
I started the thread for advice, and so it stands to reason that I should be a little more open to criticism. Your first post seemed combative to me, but I now see that while “spend wisely” can be a broadly defined category which can include many different things, it can also nonetheless mean different things to different people.

I can also see where it seems like I want to control homeless people, but you’ll have to trust me - that is not my position. At least, I don’t think I do.

I don’t believe homeless people are a like a corporation where if you give them a few bucks you receive shares or stock of their life or something like that. The money you give them does not give you any sort of voting rights or say so in the direction of their life or life choices. I would not think to ask for their “5 year plan” or an outline of their life goals or list the ways they would use the money.

They are also not children. They do not need supervision, or a guardian. They do not require someone dictating to them what they should or should not spend their money on. They do not require someone purchasing whatever items they want for them; they are perfectly capable of talking to a cashier, etc. However, I have bought items for people in the past because I wanted to use my credit card and did not want to give that out. I prefer using my credit card for most if not all purchases so I don’t run out of cash.

And of course, when you give someone money, it’s theirs. That seems like a tautology to me. And like everyone else, the needy have the right to use their assets like any other person in whatever manner they choose, essentially. I am not suggesting bringing a lawsuit or something to get the money back. I don’t follow them, I don’t confront them or shout at them if I see them buying something I don’t like, and if I saw them go into a liquor store I would not run after them, tackle them and wrestle the money I gave them back out of their hands or anything ridiculous like that.

However, I also don’t feel I resent them for spending the money I gave them in a way I don’t like. I don’t want the money back or anything like that, and I wouldn’t get upset if I saw those people again. I am not agonizing over the fact that I gave them money. It’s not like I sit at home in the dark picturing what people are doing with the money that I gave them, and just being resentful and stewing about it, bitching to myself about how those bastards are out in the world somewhere using the money all wrong.

When I want to see them use their money wisely, that is simply a hope that I have for them. Be it their definition of wisely or mine does not matter that much, but I only know of and understand what I would define as wisely. If a person asks for money in order to buy something reasonable that I did not think of or was aware of, I can respect that. On the other hand, if I were to just give money and I later saw them spend it in a way that I did not think was wise, I would be disappointed I guess, only because I would think that the money could have helped them more than it did; but I would also move on from that emotion. There is no use crying over spilled milk. In addition, I also keep in mind that many people have self-destructive behaviors, and they spend money on things they know themselves are not in their best interests. Many drug addicts know and admit that drugs have ruined their lives but they continue to purchase the drugs anyways because they can’t beat their addiction.

Let me finally say I think that past events can influence a person’s decision making process. The past events are in the past and can’t be changed, but going forward I think people can choose a different course of action if they so choose. I think that is a reasonable conclusion. Also I think each person can choose to donate to the person or charity they wish, based on whatever criteria, conditions, or thought process they may have. I think people can also determine the amount of assurance they are comfortable with that the money is supporting what they want to support. If a person who donates doesn’t want any assurance, or if a person wants a promise or a “good reason”, or if a person wants something in between the two, then that is up to the donating person to decide. Finally, I think people should be able to choose to either support or not to support activities they may or may not agree with.

You may disagree with the above paragraph. Maybe I will start a thread in the future about why people feel upset when they find out the money they donate is not being used in a way to their liking. Then it can be discussed further.

Take Care

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For anyone who cares to read, some more things I wanted to get off my chest:

I think I am (or at least was) struggling to reconcile different beliefs I have. Helping people in an effective way, (making my money “go far”), and having a reasonable amount of assurance that my money is supporting what I want it to support. I think that’s the point I’m trying to convey, so the thread title and OP is probably not written the best way. I think one of my problem was deciding one solution or one policy. But that doesn’t quite work, because people are individuals of course, so having just one single way of treating all needy people may not work in reality.

I am going to try and describe my perspective, get ready for a wall of text.

A little background: My dad was homeless from 15 to 18 until he could join the military. He wasn’t homeless because he was lazy, didn’t want to work, or wanted to live off the public dime. That would not have mattered much anyway, because when he was young and homeless social services were pretty limited. My dad was homeless because my grandfather was physically abusive, so my dad needed to leave home for his own sanity and safety. Needless to say, those few years of being homeless had an impact on him and he learned how to be thrifty and to make his money “go far”. He became very thrifty (cheap as he calls it) because that enabled him to survive a couple tough years. Joining the military saved him in a way. Even though he was homeless, and a high school dropout, and not a lot going for him, the military gave him food, shelter, income, training, an education, and self-discipline. Fast forward to today where he has been married 50+ years, retired after a long career in the government, with seven kids and many grandkids, and by most standards a productive and contributing member of society. In short, a success story. Knowing this, when I see many homeless and needy, I see them in a tough spot and could use financial help, education, or advice. (Of course as many here have posted, there are addiction issues as well as mental illnesses.) As for myself, I did not grow up wealthy and was never close to being homeless. My dad was able to provide the basics for us seven kids, and instilled in us the trait of being thrifty and making our money “go far”. Once, about ten years ago, I lost my job and was unemployed for a couple months and my need to be thrifty kicked into overdrive and it’s been a guiding principle ever since. At this point, I feel that this thriftiness has enabled me to survive, buy a house, and be debt free. There have been times when I had to ask for money from strangers before, nothing compared to what homeless people have to deal with mind you, but still I have relied on the kindness of strangers to give me money. Now when people ask me for money I can see myself in their shoes, even for a little bit, and I emphasize with them. They are in a tough spot as many have been, and I can’t logically write off all of the homeless people as worthless or condemned to a life of misery.

I remember many years ago I saw a two panel political cartoon about homeless people. On the first panel was a drawing of a guy stepping over a homeless person who was passed out unconscious under a blanket. The guy was saying “poor sap” as he stepped over the homeless, and just kept walking. It seemed like the guy just put the homeless person out of his mind, with no concern at all, and kept walking on his way to star bucks or something. The panel was labeled “Problem”. The second panel was an almost identical drawing, except this time the guy was putting some change in a cup next to the homeless person. But he also said “poor sap” as he stepped over the homeless person and continued on his way, also putting the homeless person out of his mind. This panel was captioned “Problem Solved”. It was ironic of course, and made me think, because of course I don’t think it’s “Problem Solved” just because the unconscious person has a coffee cup brimming full of change. I don’t want to be like either of those guys; I want to be more effective than that. I also want some level of assurance that my help is effective.

When I decided to start the thread I was looking for other ideas and perspectives. I emphasize with the homeless and needy and I want a course of action that is effective in some way. I want the money I give out to actually be of help. I want to determine of how much help I was actually doing, if any. It’s almost impossible to measure something like that, but I want to gauge it anyway. Whether the money is very helpful, to somewhat helpful, or is not helpful at all. Maybe it’s a useless exercise, but I like to review my actions and beliefs from time to time and put them under scrutiny. The posts here have clarified some of my thoughts about that; I am better off for listening to their perspective.

It would be naive of me to think that the times when I have given out 1 or 20 bucks that it was life changing. The posts here have helped me realize that I shouldn’t expect too much from what I give. One of the posts said that if it makes a needy person feel just a little better than it was worth the few bucks, and I can appreciate that perspective. I think that’s a pretty good way to look at it. It is probably proportional if anything, give a little and you help a little. But I would also like to think it’s of some help. I mean, if it’s of absolutely no help whatsoever to give a homeless person money than it seems like a waste of money. I think this is part of my thrifty side and I would prefer my money “go far” in terms of helping. I am reminded of Phil (Bill Murray’s character) in Groundhog Day trying to save the old man from dying. Even though Phil had knowledge of the future with money and other resources he could not save the old man: he died every time.

That was why I told the story about the time I gave money to the homeless guy who wanted bus fare. Like I said, I have never been in a situation like a homeless person, but when he asked me for bus fare it reminded me of one time I was stranded several miles from home without transportation or money. In my situation I also had to ask for money from strangers, which was an uncomfortable and awkward situation for me. The first person I asked was a woman, who appeared a little frightened because it was dark, and at night, with no one around, and she was approached by a strange man asking for money. It was uncomfortable situation for both her and me, and that is when I realized that it might be harder than I thought to get strangers to donate me the money I needed to get home. I ended up asking about 3 or 4 people before someone would give me money. But in my case, after I was donated the money it was in fact “Problem Solved”: I was able to make it back home to a warm bed, food, electricity, running water, etc. I don’t think the homeless guy was in a similar situation. Sure, he could ride several buses and travel a great distance but does that mean “Problem Solved”? I didn’t think so. Being homeless in one area and being homeless in a similar area 20 miles away doesn’t seem like an improvement. Am I Phil from the movie? Maybe. I guess I wanted more of an assurance that he was helped. I don’t know why, but for some reason I tried to gauge how much help I gave him. I guess there is uncertainly there, whether I had a truly positive effect. That is why I said I felt bad, uncertainty. It wasn’t a negative experience per se, just an experience that made me think. One person posted something to the effect that if I’m that worried about donating a couple bucks then I shouldn’t give anything and move on. That hit the nail on the head.

I asked for advice because I have been wrong many times. I am sure I will be wrong about many things in the future. I did not want to portray my actions as the most moral, or that people should act like me. I was looking for different viewpoints and perspectives, and exchange ideas. I have read the responses from the other posters and they have shed some insight for me. Some posts have been from a more libertarian perspective and some not, and I can see the rationale from both sides and have found them helpful. In particular, bronzeage’s post stood out to me the most because I could see myself doing the same things he did. I can relate to his attitude and actions, and I agree with his viewpoint and conclusion. Bilby’s post was also a perspective that made me think; the homeless probably face a higher depression rate than the general population, and a puff on a cigarette or a swig of alcohol might be enough to keep them from committing suicide for another day, or another hour, or another minute. I will keep that in mind. The advice given have clarified some thoughts of mine and confirmed others. I am thankful for the input.

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Another thing I wanted to get off my chest for anyone who cares to read...

I am getting the impression that it appears that I was beating up or disparaging needy people, so I wanted to post some of the other experiences I had to the best of my recollection. Hopefully this will add some perspective and fill in a little more of my experiences. All of this took place near the same grocery store.

*
I was inside the grocery store, shopping, and I had a few things in my cart. A guy approached me. Maybe 30 to 40 years old. Doesn’t look homeless or anything, just a regular looking guy.
“Excuse me, could you give me some money for food? I’m hungry.” he says
I notice he doesn’t have anything in his hands.
“I’ll buy you some food, go get your stuff.” I tell him
“I want something hot” he says
“OK, there should be some hot food in the deli.” I say
We both head over to the deli, and see what food they have. A lot of the hot food there gets cooked once in the morning, then sits on a warming plate all day. Buy 6 or 7 at night it doesn’t look so appetizing in my eyes. We talk about some of the food they have over there, because it’s slim pickings.
He picks out something, and gives it to me, and I put it in my cart.
“I’m going to get a few more things” he said
“OK, I will meet you in the line” I say
We separate.
I get a few more things for myself, and then I get in the line.
He comes over to me and he has a bottle of soda and what I think is candy.
“I can pay for this stuff myself” he says holding up the soda and candy
“OK”
He gets in a different line from mine.
I pay for all the food in my cart, and after I’m done I walk over to his line.
I give him back the deli food he picked out.
“Thanks man” he says
“Take care” I say

Positive experience for me.


*
Another experience I had when someone: I’m inside the grocery store, I have a cart and just started shopping. I’m looking at something on the shelf when a lady rushes over to me, also with an empty cart.
The lady is trailed by an 11 to 14 year old girl who is preoccupied with her phone; I assume the girl is the woman’s daughter.

“Read this “the lady says forcefully
The lady shoves a note into my hands.
It’s a paragraph about herself and her situation.
Struggling single mother, with three kids, health issues, paying rent, bills.
Unfortunately it’s pretty normal stuff that everyone has heard before.
But I realize something, she wrote it on a note instead of asking me in person.
She doesn’t have to speak out loud, begging to a stranger.
She doesn’t have to rehash her life story to every person she asks for help.
She is able to communicate effectively about the situation she is in, using a note so she can add more information. A paragraph instead of the normal two or three sentences. It’s not just one sentence “Can you give me some money?”
The passersby are not able to eavesdrop on us; it’s private communication between two individuals.
It’s easier for her to keep her dignity.
I think it’s clever.
Actually the note did not ask for money, or food, or anything else except for assistance. If I could please provide any assistance I could.
She is not homeless (she said she was paying rent), just poor.
“Is this true?” is all I ask
“Yes” she says
I give her a $20.
“Thank you” she says
She leaves as quickly as she came.

Positive experience for me.


*
Another experience I had with someone: I was driving in my car, probably headed towards that same grocery store. I came to a stop at a red light at a traffic intersection. It is a cloudy day, raining earlier but stopped now. It is still wet outside, the grass in the medium is still wet, and there are puddles of water on the pavement. It’s also December and it’s a little cold outside. Not freezing cold, but it’s a cold, dreary, cloudy, and wet day.

There is a lady in the grassy medium, walking up and down. She looks homeless, with an old hat and a couple of layers of old coats on. Some type of stroller bag, or luggage with wheels is sitting there. She has one of those cardboard signs – a piece of cardboard with something she wrote on it. “Homeless – please help” it says. 3 words, that’s it. I lower the window when she comes by, and hand out a $20. When I pass her the money, she gives me a weird look and pauses. “Thanks” is all she says, then takes the money and walks off in a hurry. She takes her stuff and leaves the intersection. I realize that now she has the money to do whatever she wanted to do, and she doesn’t need to stand at the traffic light anymore today. Soon enough, she is across the street and out of sight. That’s when I realize that $20 might be a lot of money to give out.

Positive experience for me.


*
Another experience was again outside that same grocery store, this time it was up on the sidewalk. The grocery store is the last store in a strip mall. Next to it is a Chinese takeout restaurant, then a Rent-A-Center, then dollar store, and several other stores. It was on a sunny Friday, mid-day, and either Labor Day or Memorial Day weekend. I was going on a camping trip all weekend, and this was literally my last stop before I left town.

I had just left the dollar store and was walking on the sidewalk when I noticed a man was lying unconscious on the sidewalk there. He was on the part of the sidewalk that was in front of the grocery store, a little past the Chinese restaurant. From the way he was lying there it looked like he had either fainted or passed out, face down with one arm stretched out, not in a purposeful or comfortable position. He was wearing what appeared to me as scrubs, thin pants and a loose shirt like a nurse would wear, and his forearm was bandaged. It looked like maybe he was homeless or poor, and had just been released from a hospital and the hospital gave him those clothes. At least that was my impression of him, but I’m not really sure. He didn’t have any bags or possessions next to him. Other people were there shopping and walking to the stores and parking lot, but nobody was paying attention to him.

I walked over to him, and knelt down and started tapping his shoulder. “Hey buddy, hey mister” I said. I could tell he was breathing, but still unconscious with his eyes closed. I wasn’t sure what to do exactly, but I keep pushing his shoulder, a little stiffer now. I pushed on his side a little too. I am hoping that he doesn’t suddenly jump up and get violent or something; I don’t know what is going to happen with this guy. A lady behind me stops and says she is dialing 911 on her cell phone. The manager and co-manager from the grocery store come outside and watch.

After a while of tapping his shoulder, the man starts to move a little and begins to sit up. His eyes are still closed. Then the man sits up, kind of like he is mediating. He is sitting, but with his head facing down, eyes still closed, arms resting on his knees. I started rubbing his back, with my palm flat and in a wide circular motion. For some reason rubbing his back feels like I am thawing him out of a freeze, giving him heat or energy or life-force or something. It seems like he is getting more conscious the longer I rub his back.

I kept rubbing his back and trying to talk to him. The grocery store managers are telling the man he can’t stay there, he has to leave. I think the man might have been mumbling something about being OK, but I don’t remember him saying anything specific. After a while the man suddenly thrusts out his hand. His arm is straight like he wants a handshake or something, and I stepped back a little. He is still facing down, eyes closed. I wasn’t sure what to do, but by instinct or whatever reason I grabbed his hand. He grabbed mine and started to pull me: he wanted some help getting up. I pulled him so he is standing up now, and then I kind of gave him an awkward hug, still holding his hand, and I patted his back a little. He finally opens his eyes, but he is still woozy. He says thanks, and I ask if he is OK. He says yes, and asks where his wallet is. I tell him I don’t know, I haven’t seen any wallets. He looks around the sidewalk a little, still groggy, and then starts walking off. He walks down a couple of stores and meets a woman there, I guess they are together. Everyone leaves. No money asked for, or exchanged; he just needed a little help.

Positive experience for me.

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*

I also wanted to fill in a few more details about the man and Chick fil-A.
The man at the chick fil-A was one of a few “bad” experiences I had with someone asking me for money. I don’t want to post the worst experience I’ve had, because I dread the right wing comments that will come from that one.

And with the man at the chick fil-A, the experience wasn’t actually that bad, more awkward than anything. To fill in a little more of the story: Some time before this happened, I was thinking that I never had an in depth conversation with a homeless person. The most I have ever talked to a homeless person was just a few sentences at most - as far as I can remember. If the opportunity presented itself, I would like to hear from their perspective and thoughts. I find I learn a lot from people when I let them talk and I listen, so I have no problem giving up some of my time if I learn something new. I would rather do that than speculate about it, and I have been on the charity giving side so to speak and I wanted to hear from the other side. So when the man asked me that day, that’s what I had in mind. It seemed like an opportunity, but I hadn’t figured out what I would say. I was going to ask another man, and a stranger, if I could have dinner with him, and I wanted to do it in a way that did not feel awkward. I am most of the time a shy person, so it’s hard for me to do. I didn’t want it to feel like I was holding his food hostage unless he said yes, or make him say yes because he was uncomfortable, or make him say yes because he owed me. I also didn’t want to interrogate him either, or judge the choices he made in life, or ask him about his long term plans or goals. Just lend an ear if he was willing; most people don’t like to eat in a restaurant alone by themselves. It was a delicate situation, and I know well enough to leave and excuse myself if it feels awkward or uncomfortable. When the man asked me for change for food I felt this was an opportunity, maybe I could eat dinner with him also. I didn’t really plan out what I wanted to happen though, and I wish I did. I had no idea what I was going to say or how I would talk to him, but I was going to figure that out on the walk to the restaurant.

I don’t know if the man realized it or not, but the body language he was using was very effective at sending a message. Like when you see a mime who is pretending to be angry or sad or frustrated, you can understand whatever the mime wants to convey using simple body language. The man’s body language reinforced his asking for money: the way the man held the change out in one hand, thumbing through it like he was counting. The message that his body language was sending was that he was a guy who was counting his money, looking at the coins and counting, and just discovering that “I’m not sure… maybe? … Yes, I think I am a bit short; I just need a little more change”. So maybe the man just discovered by chance that this was an effective way to get people to give him money. It’s more effective for him to hold out his hand with some loose change in it, versus just asking. But the thing was, when you do it twice in a row, it loses its effect and now looks like a trick. So when the man asked for money the second time, using the same body language with holding out his hand with the same amount of change in it again, and discovering yet again that “I’m not sure… maybe? … Yes, I think I am a bit short” – that felt dishonest. It reminds me of Neo in the Matrix when he sees the same cat twice. Déjà vu. Plus the fact that he asked twice for money within ten seconds felt dishonest. First he needs money for food, ten seconds later he needs money for the bus.

The chick fil-A was a short walk away, and when we got there I realized I didn’t know what to say to him. I was still contemplating what I felt, which was his dishonesty. I’m not the smartest person by a long stretch, but if I can figure out someone is dishonest in less than a minute then it’s going to lead to an awkward situation. I didn’t have a problem with still buying him food, but the dishonestly made it uncomfortable for me to talk with him. When we got inside, I told him to pick out a meal and he told me which one. Then I went to the cashier, ordered it, paid for it, and got the receipt. The way it works at chick fil-A is if it’s too busy than another person will get you your food. The cashier will only get your food if it’s not too busy. Sometimes you get a number, and they tell you to sit at a table, and someone will bring the food to your table. This time the cashier just asked for my name after I ordered and told me it would be a few minutes or something like that. So then I stepped back from the line, and was waiting and standing next to the man as other customers ordered food in front of us. As I stood there I realized I should have asked him beforehand if it was OK I could eat with him. I forgot to buy any food for myself, and it would be weird to order something again. Actually I wasn’t feeling too hungry at the moment; I was a little uncomfortable and plus I had come to the grocery store to buy groceries, not to eat. After about a minute of standing in silence the food was still not ready, and so I told him I was going to go. I gave him my receipt, and told him to listen for my name when they brought the food out. He said thank you and I left.

I left the Chick fil-A, and walked back over to the grocery store. I was in the store shopping for maybe a half hour, maybe more. When I came back outside I saw the man again as soon as I came through the doors. I was surprised because I didn’t think I would see him at all; I thought he would have moved on by now. When I had first came to the parking lot I had seen someone give him a bill, either a dollar or two, before I even got out of my car. Now a half hour later he was still in the parking lot, talking to some lady and she was giving him some money.

I didn’t want to talk to him again, so I took my cart to the right side of the door instead of walking straight out. On that part of the sidewalk there is a railing further down which holds back the shopping carts from rolling into the street. I put the cart to rest there and took my bags out, and stepped into the street and started walking down to where my car was. That is when he approached me. I was surprised because I thought for sure he would have remembered me and was stunned that he would approach me again. His hand was already out, extended, with the change in it again. Déjà vu. I wanted to make it clear that I wasn’t going to give him money, so I said “Still need more change?” or something to that effect. I am humble enough to say I was a little upset: first he is dishonest, and now he is approaching me again? Unfortunately I have the skill of finding exactly what words will be hurtful to someone. But actually the tone I used to ask that question was not angry, but more inquisitive, and so he didn’t feel hurt. His face actually lit up a little and he smiled “Thanks again mister”. I felt bad. All around not a good experience. No winners.

I not angry at him, or want the money back, or anything like that. And I still think it would be interesting to talk with him if I ever see him again, especially now the more I think about it. It’s also tough for me to judge someone in that position. Not that lying is OK or acceptable, but people will do what it takes if they think it will help them to survive. I think if I were to sleep on the streets for a few weeks or months I also might find myself compromising a few of my moral beliefs.
 
...
I not angry at him, or want the money back, or anything like that. And I still think it would be interesting to talk with him if I ever see him again, especially now the more I think about it. It’s also tough for me to judge someone in that position. Not that lying is OK or acceptable, but people will do what it takes if they think it will help them to survive. I think if I were to sleep on the streets for a few weeks or months I also might find myself compromising a few of my moral beliefs.

The person you encountered is a beggar. There are societies where begging is a recognized way to make a living. The US has never had a beggar class, so we don't really know how to deal with it.

It's not really lying, it's salesmanship. His goal is to get you to give him some money. He wants as much money as possible, in as little time as possible. It's best of his prior donors don't see him begging for more money, as you demonstrated.
 
When I give out money I feel bad because I don’t know if it will be spent wisely.

Do you feel the same way when you buy a product, giving money to a company? How do you know they will spend the money wisely?
 
I think people get upset when the receiver of their charity "misspends" the money is that the giver only has a limited amount of money to donate and they want to provide as much help as they can with that money. i.e. they don't necessarily want to help that person, but just want to help someone who needs help - hopefully the person who needs help the most. And if they had known how this particular person was going to spend the money, they would, instead, have given the money to someone else. And how somebody spends the money provides a good indication of how much they needed that money. So if, for example, you think that someone who needs money to buy food is in more serious need of help than someone who needs money to buy cigarettes, then you might get upset if your gift is used to buy cigarettes because you know you could have given it to someone who, in your opinion, needed it more.
 
I don't know why people think they should only give money to people if they spend it 'wisely'. It's rather judgemental. Either give them money or don't, but once you do, it's no longer your money but theirs. Should your boss get to decide what you spend your salary on?

Plus, if you're giving someone money because they look homeless, poor, or otherwise in need; does it really matter if they spend it immediately on food? What if they're saving up the money they get begging so that they can plan their food purchases for the next week instead? Or saving up for job training courses? Or to save up for a cheap 2nd hand car so that they can have both a place to sleep and a means of getting to job interviews. Be honest, if some bum approached you on the street asking for money so he can buy a car to go to job interviews with, you wouldn't give him money, would you? But it'd be a hell of a lot wiser for him to do than spending it on a burger at mcdonalds.

This^.

I see as something I do to alleviate my own guilt rather than actually helping someone out. The homeless largely consist of the mentally ill and drug addicts. It's not like they're saving up to get ahead. So if you do give them money, just see it for what it is, a small gesture of goodwill on your part and that's it. It will have no effect on their lives.
 
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