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It's all been said. I've seen it in action. My father loaned money to his best friend from childhood and lost everything he had to recover from that loss.
And I know a couple of people just like your brother. They charm and manipulate their way throughout life. It may be unpleasant to deal with the consequences of saying no, but I can assure you that the cost of saying yes would be much greater. Don't enable him.
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We are always more anxious to be distinguished for a talent which we do not possess, than to be praised for the fifteen which we do possess.
Mark Twain
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