Originally Posted by ngdawg

This is how I handled just about the same situation with a 'friend' of over 20 years:

"Dear..........
When I lent you that money and had you sign the note, I believed you would pay me back. I helped you when you asked. But every time I asked for some sort of payment you blew me off.
I have learned a lot these past few years and you are nothing but a negative in my life and I don't need negatives...."
And so on. She got all 'upset' but even then was her same taker self. I sued. She signed the court order to pay. She paid less than half back. I have no use for her.
Life's short. There are people who just will always be takers. They take your time, they take your things, they take your patience.
Not answering is a good start. I'd write to him, saying buh-bye with a brief why and be done with it. Don't hang around a taker/drama queen for the sake of some good memories-it's really NOT worth it.