There are plenty of examples of allegedly homeless people driving home in their Cadillacs after a long day on begging on the street.
I imagine them carefully putting their battered cardboard "Homeless Vet" sign in the trunk of their car and using the alarm fob to lower the trunk door.
That person probably bought that car, and the home that he's driving to, with money that other people gave him. Society would be outraged, if they followed him home and saw the "imposter" that he is. They would want him to be brought to justice. Stealing like that. That swindler.
Our Western Culture teaches us we must work hard for our money. It has to be honest. You must earn your money with integrity, providing a service for which you are remunerated by the system for your dedication.
(Here I'm uncontrollably laughing, because one need not beg on a street to break those rules. Look at most politicians.)
Trace this back to societal programming. To the people who make money when you're plugged into the system and you're a good consumer. You work, you eat, you buy. Repeat indefinitely until you can support the medical system in your old age.
There will always be crooked senators, greedy corporate moguls, and Madame Zeldas who stare into a crystal ball and deliver vague predictions. There will always be someone who is ready to take advantage of you.
The beggar you gave money to could actually be a homeless vet. Or he could be that guy who drives home to his suburban home and big screen TV.
None of that matters.
In any experience you have, the prize is in learning to love yourself in the doing of it.
If you gave him money, you GAVE.
It doesn't matter what he does with the money after you give it to him. That person showed up in your life---sent by YOU to YOU---to see what you would do in that situation. An opportunity for choice.
It is in the giving that you win.
You took something that you love---in this case, money---and you gave it to someone. That is a kind gesture, my friend, and I hope that you celebrate it. I am honoring you, because the entire world benefits from your simple act.
And as for lending money, the exact same principle applies here. Societal standards would mandate that you should receive the money back from the recipient. In spiritual terms, that's giving with expectations. So, if you're in such a situation, and you are feeling regrets or anger about lending money and not receiving it back, remember that having expectations is a distortion of love. Let it go. You still gave. Then see what happens. The Law of Attraction never fails.
Remember, it's in the giving that you win.
Always be yourself, all the time. Love.
You can read more about the awakening process at Are You Awakening