<p>I do not think you should do it. I think this is a very stupid idea.</p>
<p>You put your safety at risk by developing a relationship with a total stranger, especially one who is in a desperate financial situation, and even more importantly part of a demographic rumored for mental instability, drugs, and alcohol.</p>
<p>You would do more good by giving the money to charity. Homeless people are rumored to waste their money on drugs and alcohol, and while I admit this is a rumor and may be exaggerated either way, it is pretty clear to me that charities would spend the money more wisely and do more good with it. </p>
<p>I think giving the money to the homeless man has a superficial appeal, i.e. you get to see the “good” you’re doing (this “good” being an unsupported assumption). Also, people call you “noble” and you yourself think that you are “noble” because what you are doing is rare and unheard of, while charity is a common thing that often comes without sentiment. </p>
<p>But when you remove all of these superficial impressions, giving the money to charity does more good and is in the whole more humanitarian, so it is actually charity which is more noble. I am feeling rather radical today, so I will say that what you are doing even verges on the side of selfishness.</p>
<p>If you want to do more than give to charity, then there are several charitable organizations and programs you could commit yourself to, which unlike this situation guarantee your safety and considerably improve the chances that what you’re doing will actually make a difference. (One example may be tutoring a homeless man through the auspices of an existing program which does the above.) I’m sure something like this already exists.</p>