Guilt isn’t a beneficial emotion for anybody involved. It’s self-judgement and self-condemnation, and judgement and condemnation are merely human follies borne of spiritual immaturity, at least on the part of culture. It’s the depriving of yourself of receiving necessary spiritual nourishment, or the ‘holding down’ of oneself, in an attempted atonement for one’s perceived wrongdoings. In Conversations with God book 3 by Neale Donald Walsch, God and Neale have the following conversation about guilt:
Seek only to be genuine. Strive to be sincere. If you wish to undo all the “damage” you imagine yourself to have done, demonstrate that in your actions. Do what you can do. Then let it rest.
That’s easier said than done. Sometimes I feel so guilty.
Guilt and fear are the only enemies of man.
Guilt is important. It tells us when we’ve done wrong.
There is no such thing as “wrong.” There is only that which does not serve you; does not speak the truth about Who You Are, and Who You Choose to Be.
Guilt is the feeling that keeps you stuck in who you are not.
But guilt is the feeling that at least lets us notice we’ve gone astray.
Awareness is what you are talking about, not guilt.
I tell you this: Guilt is a blight upon the land—the poison that kills the plant.
You will not grow through guilt, but only shrivel and die.
Awareness is what you seek. But awareness is not guilt, and love is not fear.
Fear and guilt, I say again, are your only enemies. Love and awareness are your true friends. Yet do not confuse the one with the other, for one will kill you, while the other gives you life.
Then I should not feel “guilty” about anything?
Never, ever. What good is there in that? It only allows you to not love yourself—and that kills any chance that you could love another.
Elsewhere in Neale’s books it mentions that regret is the feeling that tells you that you do not want to do a thing again. Regret is a normal, healthy emotion, as opposed to guilt which is often employed instead.
I wrote more about the difference between guilt and regret here: To the Decriers of Anger and Regret
As for whether you should give the homeless person a dollar or feel regret about not giving it to him, if we go by the above text, it all has to do with whether that decision reflects who you really are and who you choose to be.
But personally, I think giving money to the homeless is the ‘right’ thing to do. It signifies compassion, and it’s a better use of that dollar than whatever you would have spent it on because a dollar means a lot more to someone who has almost nothing than to someone who has a place to live, water, food, clothes, medical care, etc. The amount of wealth a non-homeless person versus the amount of wealth a homeless person has entails a huge imbalance, a travesty of justice. The least you could do is discharge that imbalance slightly by giving the man a dollar.
At least it’s a better use of that dollar than what you would spend it on for yourself if you consider other people’s well-being to be as important as yours.. and why shouldn’t you? What makes you so special in the universe? What kind of a world is it where everybody is selfish and out to please themselves even at the expense of others? (I’m not necessarily implying that declining to do something charitable is “at the expense of” another—that’s arguable—I’m just saying that selfism on a collective level makes everybody hurt.) You could say that everybody has to look out for Number One first, because nobody else will, and there is some truth that, but taking care of yourself in the ways that only you can does not preclude correcting a gross imbalance of goods between you and another, and nor does it preclude significantly caring about other people on a fundamental level.
You could argue, of course, that the homeless person should get a job, or that it’s not fair that you work for that money and he would get it for free, but I think it’s idealistic to think that the homeless should just get jobs. Do you think that they live in the atrocious conditions they live in, suffering a lack of the most basic necessities of life, being reduced to wearing rags and begging on the street all day just because they’re lazy and hence prefer that to working? No, the homeless person always has some kind of psychological (or physical, or both psychological and physical) issues that make it impractical for them to work. Not everybody is cut out for the workforce; some people slip between the cracks of capitalism, and some of those people slip between the cracks of the welfare system, insurance and other such safety nets as well.
You could argue that it’s pointless to give a homeless person money because they’ll just use it for alcohol or drugs, but 1) you don’t know for sure what they’ll use it for, everybody needs a bite to eat now and then, so it’s better to err on the side of compassion than on the side of harshness; and 2) if alcohol is really what that homeless person wants to drown the pain away, even more so than the supposedly more useful things that he could spend it on such as food or soap, then who are you to say that it’s not worth it for that homeless person to spend a dollar on alcohol? Apparently, that’s what benefits him most in his situation.
You could think that the homeless person is just going to continue to be homeless regardless of what you give him and therefore you’re not really helping anything, but regardless of that the fact is that any amount of money you give will proportionately improve that homeless person’s life, even if only for that day, and that matters.