people don't pay you back - or if they do, they make you suffer in other ways. this guy called you up out of the blue. you say he's independently wealthy so he's not trying to get money out of you. maybe he's in trouble, emotionally or otherwise. you failed him too. america is a calvinist country - paying back is considered the sine qua non of virtue - but it's not the *only* virtue.

You loaned $1000 and you're getting $700 back.

Congratulations! You've just learned some of life's most important lessons, and it cost you only $300. That's less than a week's work at minimum wage.

Now you will have wasted those $300 lessons if you choose to thrown good money after bad. I'd say you have gotten off very cheaply--be thankful.

P.S.--Take the $700 and invest it in getthefuckoveryourselfandmoveonalready lessons.

Carey is thoughtful and right on the mark on this one.

LW, your friend may have hurt you when he didn't give you the money you thought you deserved, but you are the one causing your suffering now.

Never give more -- more money, more time, more love -- than you can give without expecting anything in return.

If it's a true gift, enjoy the giving.If it's a business deal, do as others have recommended and get it in writing. If you need more, it's not giving, it's not business, it's not friendship, it's just hurting yourself.

I don't want to go all Freudian here, but you may be a fixer, one of those people who got used to a parent or parents who ignored them or hurt them. You think if you do all the right things you can fix people and make them like you, so you just keep trying and trying, because you are used to the unhappy feeling it generates when you fail.

You have to be your own best friend, give yourself the love and attention and fun and support you deserve. It is hard at first, I know, but once you force yourself to take all the time you've wasted on this guy and spend it on yourself, you will consider the loss of a thousand bucks a wise investment.

Do not go into business with friends unless you can bear to lose the friendship if it doesn't work out. Time and time again, I have seen my friends make business ventures together and the friendship ultimately suffers.

Why? Because while the friendship may have come first, the business ultimately takes precedence. Agreements that you wouldn't dream of making with a neutral or unknown person are sealed with nary a handshake, because one or the other believes that their "friend" will do the right thing. Expectations are not clearly communicated, work is done that is uncompensated and very few are able to separate business actions and words between individuals from a friendship.

So I agree with other posters. A valuable lesson to learn. And it only cost you $300. I'm also not clear what you would have gotten out of the business relationship had your friend prospered. Probably not much different.

If "friend" is wealthy, then $1,000 is not much - the cost of an afternoon's amusement. And, not knowing the particulars of the deal, I might guess that he is perplexed that you'd expect it back.

"It's not a big deal" (to him).

I have a friend who rants about "Joe & Josie came over and didn't offer to pay for half of the pizza". Maybe the twelve bucks breaks the bank for her, I dunno. Frankly, I THINK THAT SHE IS INSANELY PETTY. How can she hold pizza money against her "friends"?

LW & his "friend" are ill-suited for one another. Some things need to die on the vine.

I have to say that based on the way you (didn't) list the details of this transaction, don't ever enter into this sort of thing again. It sounds very wishy-washy. Maybe its just the way you write but I have no sense of the terms of this deal and that makes it hard to say what should happen next. Cary is dead-on - use it as an opportunity to learn, not to blame anyone.

"The venture didn't go as planned, so he didn't pay me back. The amount was about $1,000, but the records are now long gone. I don't know the full details of what happened. It was never explained satisfactorily and depended on his honest dealing.”

It sounds like the LW was making an investment and expecting a payoff was a sure thing. The LW expected his friend to take care of all the details/work and then the profits get split with no concern for paperwork, receipts or taxes. But things didn’t go well (as is often the case) and the money was lost.

And now the LW expects to get paid back on a failed investment. WTF? If you invest in a business and it fails you write it off and try again. Investors don’t get paid back. There is a risk involved. No one gets rich quick without working and it’s bizarre of the LW to expect his friends and business contacts to be covering for his bad judgment (even if his friends are wealthy).

I think the LW should own up to his part in all of this failed venture and stop looking to place the blame on others. We’re all quick to blame this ‘friend’ but the truth is the guy is paying the LW back on a failed investment and that’s not a normal business practice. That $700 is a gift.

What were the terms of the deal? I don't get it. If I purchase an object at a cost of $1000 and attempt to auction it off but nobody bids on it, then I am out $1000. That was my risk, and my loss. I don't understand why the LW thinks that he is owed any money at all.

LW is darned lucky he got $700 of his $1,000 back. I invested 10K as a passive investor in a business partnership that didn't pan out, and haven't seen a dime.

Live and learn, buddy. At least I had the sense to enter into my deal with someone who wasn't a close friend.