Why I Give Money To Homeless People (And Why I Don't)

Disclaimer: This is a really insensitive post and you are probably going to think I'm a huge, snobby asshole after reading it. I'd like to remind you, please never take anything I say seriously. Except that last thing I said.

On my way to work, I always pass one of those tables with a red tablecloth and upturned water jug, and a person collecting change from the homeless. I don't usually give money to these people. (Do you guys? I'd really like to know.) I get wary when I don't know exactly where the money is going when giving to an organization, and although I don't really know exactly what the homeless people do with my money, I usually give my cash directly to them.

The man at the table that I pass each day has a low, scratchy voice, and is always harassing me to give money. At first, I would pass him and avoid eye contact. But then I started thinking, he's just a guy, and I say hi to people I see every day. So I started saying hello. Like, "Yes, you have a good day, you. But I'm not giving you any money." He started saying hi back. But eventually, he stopped asking for money all together. That's when I started thinking, "maybe I should give this guy some money." Was it a power thing? Did I want the attention? Was I just being a difficult, contrary asshole?

The thought that came to mind next, that I am a horrible person, was only reinforced when other incidents came to mind -- other times I gave to homeless people and the insincere reasons why. In my head I compiled a list of ways to get money from me if you're homeless. So print this list out and distribute it around the city, if you want me to go totally broke. I'm a sucker for all of these things:

You Kiss My Ass. One day, I was in an angry mood and I guess you could see it on my face, because when I passed a guy sitting on the sidewalk on Columbus Avenue, I heard him say in a kind, clear, Ernie-from-Sesame-Street-esque voice, "Hey miss. You dropped your smile." I stopped and gave him all the one dollar bills in my wallet.

You Kind of Sexually Harass Me, But In A Really Positive Way. Once I was walking by a guy and he said, "Damn, girl, you look good in those tights." And I gave him money. I mean, he was right, I had a really awesome outfit on that day.

You Have a Sexy Voice. Elijah, the man who always sits on my street, has a low, Barry-White sounding voice, and when he asks you for money it's like he's telling you a secret or something. Very intriguing.

You Have Really Creative Style. Props to the man in my neighborhood who wears an umbrella as a dress. He always gets some change from me.

You Display Innovative Box Architecture. I love it when a homeless person has really used their creative skills to fashion a functional, aesthetically pleasing box to sleep in. If I ever see one with a veranda or parlor, I'm going to give up, like, $100 at least. (Depending on how elaborate the design is.)

You Make It Fun. Once, outside of Food Emporium, there was a man who had a sign that said, "I just want some food." This seemed like some sort of fun scavenger hunt to me. I raced up the aisles thinking, "What would I want to eat if I was homeless?" I chose a protein packed egg salad sandwich, because I didn't want to purchase meat, a ginormous bag of unshelled pistachios (shelling pistachios is a fun way to pass time!) and a package of DOUBLE STUFFED Oreos. Mmmmm. Bon appetite!

I Offend You. Once, while in an awkward conversation with a homeless guy (LONG STORY), I didn't know what to say, and the first two things that came to mind were:

1) "It's so cold outside! I couldn't even turn the key to get up to my apartment this morning! My hands were frozen!"

Yes. My BEAUTIFUL, WARM apartment. Boo hoo for me. The man then went on to tell me that he was especially cold because someone had stolen his bag of hats and gloves. And get what I said:

2) "Maybe that person needed those gloves more than you."

Yeah, maybe someone MORE HOMELESS THAN YOU. Would you like me to kick you in the balls now?

In my defense, I was saying what I would say to my friend if they were to tell me they had something stolen. But most of my friends are not homeless and this was incredibly sensitive. This man got some money from me, but it didn't make me any less of an asshole.

You Write a Rap Song About Me And Sing It In The Subway.

You're Playing "A Whole New World" (Or Anything, Actually) On Your Accordion.

I'm Drunk.

You Have Two Little Chipmunks And You Have Trained Them To Sing And Dance Show Tunes. (Hasn't happened yet.)

You Look Like You Really Need It.

And here are the things that I won't give money for:

You Are Dressed Better Than I Am This has only happened in Italy. The Bums Wear Prada.

You Have Turrets And Tell Me To Suck Your Dick.

You Are Paying Dave Matthews On Your Acoustic.

I Just Paid My Rent. After I pay my rent, I not only feel extra poor, but I start thinking, "Hey, maybe these homeless people are on to something. Having a home is totally overrated..."