Always give it to them with no strings attached. If someone asks you for money you need to ask yourself, "If I give away this money, is this going to adversely impact me? Will I not be able to pay a bill or meet my own financial obligations?"
If the answer is, "Yes, by letting go of this money, I am going to place myself in dire straits, or trouble," then you CAN'T AFFORD to release the money. But if by releasing the money, there is no impact on your financial obligations, ie. you still will be able to feed yourself and pay your bills, then you CAN AFFORD to release the money.
If you can afford to release the money, release it all the way, don't attach any strings. Strings are, "I am giving you this money on a conditional basis, I want it back at a later date. Or, do this for me if I give you this money." Release the money all the way or don't release it at all.
If somebody says they want to pay you back, let them say it. But don't you say, "Okay, give it back to me when you can." You just let it go - FOREVER.
If someone insists that they are going to pay it back, or that they want to pay it back, I let them say it. The need for them to say that is just that, their need, not mine.
It has nothing to do with me. I always add, "I don't want it back. If I have released this to you, I don't want or need it back. It is my gift to you. If I couldn't afford to give it to you, I wouldn't give it to you. Period."
But there is a deeper and more important implication for you here. That is, in order to be able to give money to someone you choose, who is in need, YOU need to be in a stable enough, financial position to do so. It is not about giving away thousands or even hundreds of dollars. It could be a few bucks, a twenty dollar bill or something in between.
Am I rich? Heck no! But I try to live within my means so that if someone I know needs some financial help, I can provide it if that is what I want to do. To put myself in this kind of position, places the onus or accountability/obligation on me to try to have my financial house in order.
When you are always trying to make ends meet, struggling from paycheck to paycheck, that is not a position of power. Although we are all beholding to someone, at some level, be it our boss, our company, our spouse or whatever, it is possible to have some financial autonomy and independence.
It is very important to get yourself in a position so that in the least, YOU won't have to ask someone for a financial helping hand. It is simple, but not easy to do.
To release money to someone who needs it and to be able to do it with no adverse financial impacts to your wallet, is a gift that you create for yourself.
You honor yourself by not having to be indebted to others for stuff that has long lost it its value. More importantly, you give yourself the gift of freedom which in turn enables you to provide financial support for others, in the form of releasing money to them. Money that you have said, "Goodbye to", always and forever.
You see, we are all connected. And you never know whose life you touch or who you help. Contrary to the actions of so many people, when you help someone else, you truly benefit - you do not lose in the long run. That same person you helped may not come back around and do the same for you, but that is not the point, now is it.
Do the world a favor. Get yourself in a position so that you can release money. I have heard and seen it written that if you love something and let it go, if it is meant to be, it will come back to you. I say the same thing about support. When you release and give support to others freely, in the form of money, with no strings attached, I believe that it always comes back to you.
Beauty is as beauty does. Do it, you beautiful creatures, you!