Really, you're better off just letting it go and counting it as an expensive lesson learned. You never, ever LOAN money to friends and relatives; you GIVE it and expect to never see it again. If you happen to get repaid, it's a pleasant surprise.
I like that idea. It's great advice I got long ago.
Offer to give 10% of whatever is asked and don't expect it back. This usually chases off the person asking for the loan but if it doesn't at least you can close the door on it forever.
"Hey, I really need $100, I can pay you back next week."
"Tell you what. Here's $10 you can have and good luck to you."
I've forgotten some loans from my past that aren't ever being repaid (generally pretty minor ones a few 100's of $$$) and I sleep well at night.
There are *no* solid repayment assurances from anyone. The moment your money is gone, it's gone.
Somehow I'm reminded of the episode of the Sopranos where Artie tries to get his loan back from the goon who was running the crooked wine startup. In the end, of course, you need a guy like Tony on your side to collect!