I was slightly lost on Gaffey St. in San Pedro and stopped to get my bearings. It seemed a coincidence that the homeless woman I’d passed a block earlier was heading my way, until it was clear she was zeroing in.

As she asked me for spare change, I couldn’t help focusing on her mouth. She was filthy all over, every visible inch of skin besmirched with grime, her hair a ratty tangle. But it was the mouth that magnetized my gaze, the teeth, those blackened stumps of rot—a telltale signs chronic meth use. This poor soul had hit bottom and fallen through, and my pessimistic sense in the moment was that there was no recovery in her future, that this was her lot in life for as long her body could endure.

But she was alive now, in front of me, asking for money that in some tiny way might ameliorate her suffering for a trice. I handed her a dollar, as I do almost automatically when panhandled. She snatched it with the aloofness of an orangutan accepting a banana and turned on her heel, making a determined beeline in the opposite direction.

I followed her at a discreet distance to see what she was about. She crossed the service area of the first gas station she came to and went up to the pay window, where she purchased a pack of cigarettes, unceremoniously peeled off the cellophane and discarded it to the ground, pulled a single fag to her lips, and lit up. She ambled off more slowly than she had come, on her way to an unenviable future.

I found myself annoyed that I had been such a soft touch. I don’t especially care what people put into their own bodies, but I’m not crazy about my money funding Big Tobacco, even indirectly. And while I’m not looking for gratitude when I give, the whole episode, from the littering to how unmistakably I was no more than a means to an end, left me sour. Maybe this was one time when I should have said no?

It’s a few weeks later, and I’m in a Belmont Shore bistro having coffee, when in walks a man who immediately seems out of place. Far less bad off than the woman in San Pedro, the man was just as easy to identify as homeless, right down to a certain affect of disconnection and mental imbalance that occurs far more frequently in the homeless population that in society at large. He would stand contemplatively for a few seconds, then take a few steps forward and again seem to engage in contemplation of nothing in particular. In this fashion he made his way to my table and asked for money with a quiet brusqueness. I declined—as I invariably do within a place of business (something about my feeling that patrons have a right to be left in peace to enjoy their purchase, along with the fact that businesses generally don’t want their patrons to be bothered in such a way—a practice that giving in such a scenario is likely to encourage).

He hovered for an uncomfortable few seconds, then moved off to another table, interrupting a conversation between two men. One was silent, but the other offered to buy his tableside supplicant a cup of coffee. I was guessing that this was going to be a case of “no good deed goes unpunished,” so I tried not to stare as I attended to what came next. It wasn’t what you’d call a row. Contretemps is more like it.

“He asked me for change, but I literally didn’t have any,” Anthony Shadduck, the customer who decided to give to the man, said later. “I had some bills of larger denominations, but I wasn’t going to hand him a five or a twenty. […] He kept standing here, and I thought, ‘Oh, maybe he wants a cup of coffee.'”

Shadduck explained to me that typically when he is asked for money in or near a place that sells food or drink, he will offer the supplicant a foodstuff.

“When it comes down to it, a cup of coffee’s not that much money,” he says. “And I always think, like, people have a right to eat something. Even a cup of coffee. So I’ll offer, because I feel like I’d like [if I were in need] someone to do the same for me.”

But as soon as they approached the cash register, Shadduck started to get more than he’d bargained for.

“He said, ‘I want an espresso, a cappuccino, whatever that shit is,”” Shadduck relates. “I [thought,] ‘Well, that’s $3. But whatever. What’s $3?’ Then he was like, ‘What about something to eat?'”

From there things got worse, as the man complained about the cup containing his beverage, changed his mind about the food he wanted, and was rude to the employee serving them.

“He started ordering the barista around,” Shadduck says. “First of all, he didn’t like the cup it was in; he wanted a ceramic cup. But then he didn’t want that, either, so we transferred cups twice. And then he didn’t want the cookie he wanted before; he wanted something bigger. And I was like, ‘Dude, I’m a musician, and I don’t have a lot of money. I was just trying to be nice.’ Now I felt bad, because I didn’t know he was going to start a scene. I was like, ‘Shit, I started this. That was stupid.'”

After about five minutes the order was finally squared away, and Shadduck went back to his conversation, while the man sat to partake of Shadduck’s generosity. When the man left, spilled sugar was all over the table, along with a small collection of trash (empty sugar packets, stirring straws).

Shadduck admits to being a soft touch. And, like me, he’s not always pleased with the results.

“I always think: Everybody’s got their preferences,” he says. “Even if they’re down and out, even if they have certain issues or whatever, people still have preferences. So I think I should honor their preference. I would want someone to honor my preference, you know? But if it gets to a certain point, I’m like, ‘Dude, this is what you’re getting. I literally got up out of my conversation to get you a cup of coffee.'”

Christmastime raises the profile of a constant question: When to give, and how much? Generally (if not universally) speaking, giving is a mitzvah, so even if one is justified to deny a request for money, food, etc., is not giving ever really better than giving?

I’ve had many conversations about this topic and heard many people answer that question in the affirmative. But every time I listen to a philosophy attached to such a position, it strikes me as more of a rationalization than a proof, an instinct of not-giving with an a posteriori explanation of why that is the better choice.

I wouldn’t go so far as to say that giving is an obligation. I’m even open to the possibility that in some circumstances giving might be…a mistake? misguided? There is no way I can finish that sentence without feeling squeamish, but let’s got with it: Sometimes giving is a mistake. When it comes to giving, isn’t it better to err on the side of giving too much or too frequently than not enough?

Maybe Anthony Shadduck made a mistake. In exactly the same situation, I chose not to give. But I’m not proud of myself. I’m not here to brag about my wisdom in denying this fellow human—clearly a have-not on a street full of haves—what was a meager request even in light of however rude and high-maintenance he may have been.

Let’s not overanalyze it: As a rule, giving is good. And even if there are exceptions, they’re not reason enough to play a different game.