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I used to loan my friend cash fairly often. Sometimes he'd pay me back quickly. Sometimes it took a while. It was never a stress on the relationship.
I looked at it as if I was GIVING the guy money, so I never worried about getting it back.
My friends are few, but they are GOOD friends. I would do just about anything to help them out, and they'd do the same for me.
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Ass, gas or grass. Nobody rides for free.
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