Life would be much easier if people could be honest when they need money as opposed to the acrobatics involved in it.
Folks just need help sometime.
When someone asks for money, and I wish to help, I do this.
I say....
"Listen carefully to the following, I want you to decide if this is a gift or a loan.
If it is a gift, then someday pay it forward. But if you decide it is a loan, you need to tell me the exact date you will pay me back in full. No installments. No late payments. I don't care what date. It is your responsibility to remember. Not mine. I wish not to be encumbered by your debt."
Most folks get this.