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Today a very good friend of mine texted me, asking me to lend him some money. Normally I don't hesitate much if the amount is acceptable since he is a really good friend. We have a long history of friendship and our homes are very close to each other. But I was still shocked when he asked for 20,000 dollars. 20,000 dollars may not be a very huge amount but it is not a small amount anyway. I never mean to doubt him. I believe him. I really do. But I had experienced several times when some "friends" borrowed money from me and they never bothered to pay back, and I was too ashamed to ask my money back. It was just several thousand so later I decided to just let it go. When it comes to this amount, these memories start to haunt me. I was quite panicked when he asked for loan from me and somehow I said yes. But now I start to worry. I wanted to keep my promise but I also worry about wasting money and losing friendship at the same time. But if I don't lend this money to him, our friendship is still at risk. He said he is going to pay me back after a while (he didn't specify when). Then I did a little calculation based on his earnings, and the numbers don't really match. It literally will take ages for him to accumulate this amount of money. So...I would like to hear your opinion about this situation. Should I lend him money or not? I am feeling quite guilty now because somehow I sound like not trusting him. Does this really make me an awful friend? PS: I did ask what he need this money for. He said he bought a house but he used his credit card for his down payment. He has to pay back this money before the interest-free period expires.