Lending money to friends...

[C33]

...how do you deal with it?

This question is being prompted by an unfortunate friend's situation:
He lent a substantial amount to a trusted friend, she is a good, honorable person.
His financial circumstances have changed and he is now in bigger need of that money than her, she has a comfortable retirement and is not under financial stress or likely to be homeless.

He did verbally agree to lending her the money until she sold her property, but it's not looking like it is likely to happen:the selling price is much higher than the market can bear.

He hasn't heard from her in a while, even though he contacted her upon her return from vacation.

He has a check given to him by his friend, she was holding money his brother owed him.He told her to keep it, as a loan, in a time when she needed money for moving expenses. He kept the check, just in case.

The friend bought a lot of high end items with that money,I know her and she has expensive taste. She is a great person and worth helping, and he is feeling bad for cashing her check. However, he hasn't heard and is in red in the bank. I haven't heard from her either, but the circumstances and bond are different.

His choice is between honoring his word and not cashing the check or...borrowing money from other friends...like me.

How do you discuss changing your mind about that sort of things?

[{aspiring_to_clarity}]

Never loan a friend money, consider it a gift.

Now that the dead is done however, I would suggest he contact her and let her know that he is in financial straits and ask if she is able to repay all or a portion of the money he lent her.

There's no harm in asking. Even if she cannot repay it he is no worse off than he is now. I doubt that a polite request couched with the reasons he is in need of repayment at this time would be hostile to the friendship. I would hope not at least.

[cdn2wheeler]

Aspiring has it right on. As long as the request is submitted with respect and without self-pity, there's absolutely no harm in asking. Maybe the request could be made to pay back a certain percentage over a period of time instead of asking for the full amount back right away.