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Do you have emails or your cancelled check to him to show that you loaned him the exact amount and that you never received payment? Those alone would hold up in court, though signed documents would be better. Even an "IOU $1000" with both signatures holds up in court. Small claims court, anyway.
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"Without passion man is a mere latent force and possibility, like the flint which awaits the shock of the iron before it can give forth its spark."
— Henri-Frédéric Amiel
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