I saw the young man sitting on the bench. He looked scruffy, with uncut hair, tattoos and piercings. He looked like hadn’t slept well in a while.

To get where I was heading, I had to walk down the narrow passage between the two buildings and past the bench. It was unavoidable.

“Can you spare a dollar so I can get something to eat,” he said to me.

I made eye contact, so I had to stop. I briefly hesitated, then pulled out my wallet. The moment where I could have made a graceful exit had passed.

My wallet had no ones. The smallest bill was a five. I pulled it out and handed it to him. “You’re in luck,” was all I could think of saying.

“Thanks man. I really appreciate it,” he said.

Giving away money is uncomfortable.

I do it often enough–last year I claimed over $1,000 in tax-deductible contributions to charities–but these face-to-face encounters still leave me with a weird feeling: I have money and you don’t; you are asking me to give you money, perhaps embarrassed for doing so. I have the power to decide to hand over some cash and whether to ask for something in return, perhaps wondering how it would be if roles were reversed. It is a transaction, and not really a person talking with another person at all.

We give large sums of money unconditionally to family. We give small sums of money unconditionally to strangers. Everything in between is weighted with social awkwardness. How much are you asking for? What do you want the money for, and why do you think I can give it to you? Are you a blood relative? How well do I really know you? Is this a grant or do I expect repayment? If I give you this money, do I expect you to do something  in return?

Money talks, as the saying goes, and it can say both good things and bad. My mother has told me more than once that she gave “a large amount” of money to my sister, and that she expects it to be paid back. My guess is that it is in the several thousands of dollars. My sister’s past history warrants a cautious approach to money lending. She defaulted on a loan for which my dad was a co-signer, for instance, something he still feels stung by. She accepted gifts of money and stuff over the years that is now gone: spent, lost, stolen, sold for cash, or just destroyed.

So my mother has some justification. But we give large sums of money unconditionally to family, right? Perhaps not, after family has burned you once too often. I may still be naïve about such things; I hope I am never in the position to have to make that choice.

My mother doesn’t really need the money–it is on principle that she is asking for repayment. My sister doesn’t have it to repay.

It is a stalemate.

Meanwhile, I go to my job and give of my time; my company pays me in return. I give to charity, I give to panhandlers. I intend to ensure my children’s college is paid for. I worry about having enough money for retirement. Life is measured by a series of transactions.