Dear Mrs. Riches:
I have a friend, "Saul," who went through a rough patch nearly two years ago. He'd lost his job and his girlfriend at the same time and it took him some time to get back on his feet. I invited him to move in for a while, making it clear how we would divide up daily living costs like food, cleaning supplies, and take-out food. We also discussed rent for his room and agreed upon a fair amount per month. He stayed for six months.

While he lived with me, he never had any money, always saying, "Add it to the tab." I, in fact, did keep a tally of the expenses and told him the total -- about $2,400 -- when he moved out. He promised to pay it back after he'd been in a job a little longer. After a few months of being on the job, I brought it up again. This time there was another excuse.

I'm not broke but could definitely use the money. I'm starting to think I'll never see it, though. Do you have any good advice?
--Just Call Me "Patsy"

Dear Patsy:
If "good advice" is the kind that definitely gets you your money back, then, er, can we bargain it down to "adequate"? I can offer suggestions, but I think they may all come out sounding like condolences. Or perhaps, to honor National Poetry Month, we could write an ode to your lost dollars. That might provide the only smile to be had out of the whole messy situation.

You see, here's what I'm worried about: I'm afraid that Saul's former employer and former girlfriend may have known a thing or two about him that you didn't. Perhaps that's why each of them broke up with him in their own way. But lucky (and kind) you, you offered him a haven where he could lick his wounds, get takeout Chinese, and chalk it all up (and rather flippantly, it sounds) to a tab. The fact that the tab was coming out of your hard-earned dollars was easily attributed to your charity and friendship.

He didn't help you for six months, then didn't pay up when presented with a real list of the real money you spent on his behalf. It doesn't sound like he even offered to pay in installments while getting his new career underway. That might be because he knows another disaster is around the corner (otherwise known as a pattern of behavior).

But I don't think you have to give up just yet. I would ratchet up the tone a notch (or five) since, so far, you sound so darned reasonable about the whole thing. Try sending an official-sounding letter that spells out deadlines for when you expect your money.

If you're over his friendship and just want the money, back it up with a promise to file in small claims court for the bill if he's late. Whether you follow through at that point is up to you. (He will, knowing you to be a patient, very understanding friend, most likely think you won't go through with it.) That's precisely why I would file. $2,400 is no small potatoes, but this guy cost you something even more precious; he tarnished your giving heart.

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Fool contributor Elizabeth Brokamp is a licensed professional counselor who regularly talks money with her honey, Robert Brokamp, editor of The Motley Fool's Rule Your Retirement newsletter. To get your money and relationship questions answered, send her an email.