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What you could do is go to a restaurant/store and tell him that you're buying, then when it comes time to pay just tell him to give the cashier your $100. Gives him 0% chance of lying his way through it because 14 year olds are awkward and it would be incredibly stressful. You could judge his reaction to make sure he really did it and then he'd be so incredibly embarrassed he'd probably immediately apologize (if this is a good kid).
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I found the thread the weird young freak meant to post this reply in!
http://forumserver.twoplustwo.com/showfl...;gonew=1#UNREAD