Quote:
Originally Posted by Ankimo
Your friendship with this person is already on the verge of ruin. So give it one more shot and tell him that if he doesn't start paying back immediately, you won't hesitate to inform all your mutual friends.
If this doesn't move him, move on if the money is insignificant to you b/c the mental stress just isn't worth it. If it's a large amount of money to you, stop being a pussy and threaten the guy in some way.
He's not worthy of being your friend if he can cheat you over money so better to find out now rather then invest more years being his friend.
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This.
When you first approach - do it somewhere neutral... don't just jump straight into it. Do a social activity together like you guys have done in the past as friends.
Maybe have a beer or too, diner, etc have some laughs first, show genuine concern for his well-being - he will reciprocate - and then make a gut call on how to advance... don't be afraid to eventually go over to his parents house with evidence of how you've given him money and see if they will pay up once it seems like you have to write off the money.
Also, here's 5 rules for poker an old timer gave me in my first poker game. Something to consider for the future, re 1 & 2, so you dont find yourself in a similar spot again.
1. Be careful who you befriend
2. Never lend
3. Never borrow
4. Never sweat it
5. Be classy