Oy. I've had a similar experience with my younger brother. However, he has since come to his senses, and has pulled himself out of his self-administered trench. He claims that, while he was a fool in taking advantage of me while I helped him, he never would have made it through his own period of prodigal desert wandering if I hadn't been there. He has paid me back every cent I gave him. I'm proud of him. I would do it all again, too.

Hope it works out.

I know the feeling exactly. I've got two siblings that are...perhaps a kind way to put it would be "less than responsible."

I wouldn't loan my sister anything unless I planned on never seeing it again.

advice about money and relatives and friends for that matter.

When helping someone out....do it as a gift and not a loan. Chances are you will never see it again.

I once loaned my sister a considerable amount of money, fully expecting that I'd never see it again.

I'd forgotten all about it when she surprised me by offering me a motorcycle in lieu of cash as repayment. VRRRMMMMM.

Oh, money loaning in the family is a strange deal. Sorry you had to learn the hard way. I learned the hard way too. AWTM has a good way of thinking about it, and it's true.

My take on loaning money: ask for collateral up front - preferrably something you wouldn't mind keeping.

Remind me not to borrow money from Herbey... he wouldn't like what I'd give him for collateral!