Home from college one year during spring break, a friend and I drove into the city from Brooklyn one night to hit up a club downtown. Both flat broke at the time, I remember we had exactly one ten dollar bill between us, which we planned to save for a late night feast of dirty water dogs at Gray’s Papaya. Just as she nailed her parallel park but not before turning off the radio and engine, a reasonably normal seeming, preppy looking gentleman with a clipboard got up off his stoop and approached me on the passenger side of the car.

It was the mid 90s, before cell phones and the internet were really a thing yet, so approaching strangers on the street with a clipboard if you looked normal, even in New York, was a perfectly legitimate way to engage in activism. He said he was collecting signatures and fundraising for an AIDS charity. I forget the particulars of his pitch and the ways in which he managed to sweet talk me, but before I even knew what was happening, I was reaching into the pocket of my suede fringe vest and handing him the ten dollar bill through the open passenger side window. I didn’t need to look over and see the murderous look on my friend’s face to appreciate the gravity of what I’d just done. I’d willingly handed over every last penny we had to a complete stranger. Our hot dog money. Gone.

Point being, I’ve always been a sucker for a sob story. Years later, I almost defaulted on my student loans because I became convinced that the root of all my problems in life stemmed from the fact that I wasn’t tithing my income. So I signed up to be a Partner in Hope at St. Jude’s for ten percent of every paycheck, in spite of the fact that my finances were a disaster and I was still flat broke. Another time I hit up a horrified coworker for some cash in Battery Park to buy a homeless guy a beer. Shirtless and barefoot, he’d just finished shouting a rendition of The Beatles “Piggies” at the Wall Street dudes walking down Whitehall Street as we ate our lunch.

When we made eye contact and he accused me of thinking he should “just go get a job,” I admitted that it was not the case, as I had a job myself and was out of my mind with misery. He sat next to me and dropped the crazy act, and we actually had a lovely conversation about life and work and the depressing choice between being free and destitute or trapped in corporate hell in order to get by in the world. I felt the least I could do was buy him a beer after he’d opened up to me about his life and made me laugh with his performance, and I just assumed my coworker felt the same way. But when I asked her to spot me the cash until I could get to the ATM, it was like I’d told her I’d decided to elope with him.

I don’t really know why I’ve always felt a personal sense of anxiety over the plight of the homeless in particular. I used to think it was run of the mill Catholic guilt, but then virtually all of the other Catholics I knew were as selfish and uncharitable as anyone. From being called a gullible idiot to hysterical warnings about how getting close enough to a homeless person to give them money would “get me stabbed” one day, the most common refrain against extending any sort of charity, no matter how small, to a down and out fellow citizen was that they were just going to “use it to buy crack.” Or speed. Or heroin or Colt 45 or whatever other inebriate a homeless person could somehow magically procure in a metropolitan area on the tidy sum of a dollar. Because you know, there were dozens of mythical documentaries and studies, none of which anyone could ever seem to name with any certainty, just proving that when given a choice between getting a job or begging for money on the street from the upstanding citizens of humanity, the homeless person would always choose the begging. Every. Single. Time.

It was pointless to try and explain that handing over a couple of dollars in exchange for a heartfelt “God Bless You” made me feel good, or that I didn’t in fact know that they were going to use my money to buy crack. Maybe today would be the day they used the money to buy food. They must be eating at some point, otherwise how were they still alive? Or maybe, just maybe, a tiny sliver of compassion from a stranger, no matter how fleeting and insignificant, could simply brighten a homeless person’s day. Or make them feel like an actual human being for a second, visible and present and as worthy of being seen as anyone else.

But also, so what if they did spend the money on drugs? Wasn’t the point of giving to do it freely — without judgement or expectations on my part? Once I handed over the money it no longer belonged to me, so what right did I have to presume to dictate how it should be spent? And at the risk of pointing out the obvious, I imagined that life on the streets was really depressing, whether one “chose to be there” or not, so I can’t really say I’d blame a person for choosing to get high.

But none of my rationalizations mattered. Because in my pathetic and misguided attempts to assuage my own guilt and contribute anything towards a problem that seemed cosmically unsolvable, I had become part of the problem. The dreaded enabler. The delusional and tone deaf bleeding heart, tossing rusty pennies into the proverbial abyss and getting dismissed and laughed at by both the homeless and the “normal” people.

I don’t really give as much as I used to, mostly because I hardly ever carry cash anymore (or so I tell myself.) But then a few months ago I withdrew 20 bucks from the ATM on my way home from Rite Aid and gave it to a homeless guy in the parking lot. Not because I felt guilty, or thought it would change his life or incite a Christmas miracle that would launch him on a path to healing and wholeness. I did it because it was the day before New Year’s Eve and I was feeling good. And also because frankly, I just felt like it. I’ve realized that if my only two choices in life are to either enable a broken person, or to fall in line with a society that proudly doesn’t care, I’d simply rather err on the side of the crackhead.