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the way i see it is friends and money do not mix. unless its like hitting me up for a $20 so you can buy some beer or something. i only have 1 friend that i would lend that kind of money to. he is the type of guy i can count on for anything. this friend of yours doesnt sound that close to you.
like mentioned above...if you can stand to lose it and NOT hold a grudge or have this feeling in the bottom of your gut everytime you see him pull his wallet out and hand his $$$ to someone else instead of paying you back then lend away. if not pass.
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