At 3:00pm on the last day of the decade, someone on the street asked me for money.

This happens to me relatively frequently here in Long Beach, as I imagine it does to any passably-dressed adult in any big city in the United States. This gentleman’s approach, though, was a bit unusual. For starters, he appeared no more destitute than I. He began with a simple, “How are you today, sir?” as he passed by the sidewalk table at which I was just sitting down to read. It was not until he had stepped nearly 20 feet farther that he resolved to importune me further.

I followed his story only generally, since early on I realized I had no way to confirm its veracity: he talked of a fire that had destroyed his apartment building the previous day, of how little cash he had on hand. He seemed to well up several times, speaking of how it went against his grain to beg anyone for anything, but that now he found himself with no other option. He said he did not want money, but that he had resolved to try confiding in one person to see if that individual might buy him a meal to take back to his wife and daughter in the motel at which the VA had temporarily put them up.

Was I being had? I have no idea. I don’t pride myself on being a great reader of people. Whatever the case, I once again found myself wrestling with the question that overarches any situation of this type: When to give, and how much?

At this point it might be worth noting that I am near the antipodes of affluence, able to maintain my quasi-bohemian existence only by way of good fortune: enough family support to supplement the paucity of gainful employment I can both scare up and tolerate (call me an ineffectual and fragile soul), along with being someone of relatively modest needs and with an ingrained parsimony. So for me the concept of ‘disposable income’ is far more abstract than concrete. Nonetheless, I can afford to give, at least on occasion, however meagerly.

In one sense I am what you might call a soft touch. I have no patience for the argument that it’s somehow better for society as a whole—and even for those experiencing verifiable financial hardship—not to give, that giving money to people in such a condition (and more broadly, to social-welfare programs) actually perpetuates the problem(s). If you’re hard up enough that you feel the need to ask me for money, my instinct is to want to give you something. I don’t say this makes me a swell guy; it does mean, though, that I am not completely lacking in empathy. By some set of minor miracles I have never found myself in such need (well, if you take my parents out of the equation), and I am fully aware of how awful it would feel to find myself in the position of having to approach you on the street to see if you can spare some change. Awful.

For all that, rightly or wrongly there are factors other than my own means that give me pause. Example: Once in the parking lot of the East Village Vons a woman responded to the small handful of coins I gave her with unmasked disdain. It’s not that I demand gratitude, but I was certainly, if not offended, miffed at her response. “If you don’t want it,” I replied to her glare, “you can give it back.” (Needless to say, she did no such thing.) Then there are the many times I have been accosted by individuals whose brusque and even aggressive “requests” seemed to speak more of a sense of entitlement than wounded pride, who regarded me as if I absolutely owed them something. Additionally, I am not so naive as to believe that everyone who asks for money is in genuine need.

And so, that compound question: When to give, and how much? During the course of my life I have tried various approaches. Once upon a time I always said “no,” then chose to give or not give depending on the response I received. During another period I would tell the requester I would give him or her something, but that first I’d like to talk with him/her a bit, desiring to hear about what brought him/her to this juncture (the intent being not to force the person to justify him-/herself, but rather for him/her to know I considered that person as a distinct individual and not merely a “homeless”). Then there was the epoch in which I would never give money but sometimes offer to buy the person food. (I’ll never forget the poor fellow who chose a box of children’s cereal from the grocery store into which I accompanied him, then asked if he might also have a cantaloupe, as he hadn’t eaten one in a very, very long time.) On occasion I have tried giving larger amounts of money than I could really afford to part with. One New Year’s Eve that I spent depressed and alone wandering downtown Fullerton, I thought it might be worth giving the sadly filthy man I encountered pushing a shopping cart full of I-don’t-know-what a $20 bill and the last of my Jack Daniel’s, in the spirit of raising my own spirits by this fiscally-irresponsible (for me) act of benevolence. (I’d be lying if I said it worked: I was still depressed, only now $20 poorer.)

Exactly a decade-and-a-half later, no longer with a guiding strategy to help decide such encounters—sometimes I give money, sometimes not; now and again I will fetch food from my apartment upstairs when I find someone hovering around the dumpsters at the back of my building—I listened to one more story. And honestly, I didn’t want to have to make a choice; I just wanted to enjoy my last chance to read in 2009 before heading over to Trader Joe’s, then out for New Year’s Eve. I explained to the man that it would be “easier” (a flare-up of shame causing the word to stick in my throat) for me just to give him a couple of dollars, easier because I had little money myself and buying him a meal would cost significantly more. I didn’t mention that I did not want to expend the time and effort it would take to procure the meal, nor to risk more of an outlay of cash (i.e., in the event that I was being hustled). He most graciously and gratefully accepted my proffered George Washingtons, the equivalent the Americano waiting for me by my book. He pressed my hand, told me I have a good heart, told me he’d never forget me. “Listen to me,” he said: “Thank you. Do you hear me? Thank you.” Over two dollars and five minutes of conversation. I wanted to crawl under that table rather than be subject to such unwarranted praise.

Later on, walking up Pine Ave. from that ridiculous rally-car jump thing (I’m like a moth to a flame when it comes to large crowds congregating within walking distance of my home) to the first of two parties I’d be attending that night, amidst the general revelry, I espied a homeless man I see from time to time taking shelter under the entryway of a couple of closed storefronts, standing, reading a tabloid, seemingly oblivious to the wealthier world walking by. I have often ruminated on the unjustness (in a conceptual constellation of unjustness) of the assured fact that if you’re homeless and are unwilling to ask for help (because you’re too embarrassed, because you don’t want to impose upon anyone, because you’re simply shy, because in such an abject state rejection is spiritually unendurable), you will get less than those willing to ask—unjust because, in my worldview, need should dictate aid, not assertiveness. “Excuse me,” I said, startling him, “could you use this?” He snatched the five-dollar bill from my outstretched hand. “Thanks, bro!” he answered, barely audible above the hubbub. It struck me as a response far more appropriate to the gift than the one I’d received earlier, closer to what I deserved (if ‘deserve’ has anything to do with it).

This has not been a story of what a great and generous guy I am; I claim no such moral authority and freely admit to being perhaps too heavily invested in my personal subset of bourgeois desires. I am just someone who is not nearly as unfortunate as many people I encounter on a regular basis, and who struggles with the question of how I ought to act from such a position. And I have no answers. I am just muddling my way through.

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