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Loans; Credit; Debt

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A friend of mine who is known to burn money and not repay loans is continuously asking me for a loan. I have heard that one should always give a loan when asked. Should I be giving him a loan?
I have done everything in my power to pay back my debts, but every time I make a little headway, something happens to plunge me into debt again.
Your friend gets to make her purchase and you get to rack up some points. Kosher?
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