My son's best friend entered a homeless shelter a few weeks ago. He had been forced to leave his father's house after it was sold. I drove him to the shelter and, when I dropped him off, I gave him $20 for bus fares and to help him in the transition. (There is no cost for the shelter.) He promised to give me the money back after he got a job. Well, he got a job over a month ago and still has no expenses to speak of (the buses are now free). I have been hinting to him and his brother that it might be time to pay me back, but so far there’s no real response from him.

Should I press it? Should I wait until he is out of the shelter and on his own? How long should one wait before asking more directly for the money back? Should I even ask at all? It's a small amount, of course, and I feel kind of bad asking for it, but that was the deal. The fact he has never brought it up since getting his job makes me feel he has no intention of paying me back, which makes me feel bad. I don't want this to be a sticking point, but don't people in bad circumstances have some obligation to repay their debts, especially since they volunteered to do so?

Name withheld

Dear friend,

The amount is small, but it’s easy to relate to your discomfort. It’s also easy to imagine that there’s a lot more going on here. Let me restate the main facts. Your son’s friend used to have a home – his father’s house. Now he doesn’t: first the house was sold and then he was forced to leave. Now he lives in a homeless shelter. You were kind enough to drive him to the shelter and to give (your word) him $20. He promised to give you back the money after he got a job, but he didn’t say how soon after he got a job. He got a job a month ago, but hasn’t, despite hints, given the money back.

Should you press for repayment? You should – now and always – do what you think is the right thing. My perspective is that you should not press for payment now – if ever. The amount of time between your giving him the money and his promising to give it back may have been mere seconds. But, though you say the repayment promise “was the deal,” it seems clear from your letter that he did not ask for the money and his promise was not a condition of your gift. As far as I can tell, his promise was, legally, without “consideration” and therefore unenforceable.

Of course, people honoring promises they make without consideration is an important part of human civilization and relationships. But I would urge you to consider this fellow’s circumstances at the time of his promise. I see nothing in your letter to suggest that experiencing the sale of his father’s – and his – home, being forced to leave that home, and becoming homeless were not hugely stressful and daunting events in this fellow’s life – particularly arriving at the shelter the first time. For his sake and yours, I would urge you to assume that he is an honorable person. That he still lives at the shelter hardly makes it unreasonable, let alone irresponsible, for him to save his earnings for the day he can leave the shelter for a new home – and to assume that you will wait for repayment until after he can do that.

You have the opportunity to model to your son’s friend, and likely to your son – and most importantly to yourself – graciousness and generosity. If you take that opportunity wholeheartedly, I expect that your anxiety over what to do about the $20 promise will evaporate and you will be much more likely to have a grateful friend for life.

Leeland Cole-Chu is a retired judge from Salem. Write to him for advice at afriend@afriendsthoughts.com.