I struggle with charity. It’s just not… me.

Don’t get me wrong. Thousands of organizations across the world do unbelievable things on a daily basis and I try to give what I can to the organizations that are important to me. And I’m not here to tell you to do otherwise.

But when I thought about “donating”, “giving”, or “volunteering”, most of the goodwill that came to mind felt like regimented, wholesale acts of kindness that sometimes lacked authenticity and a heartfelt, human component. Pouring ladles of soup into styrofoam bowls for a line of homeless people and writing a check to JDRF for their Type 1 Diabetes research were no doubt beneficial acts of kindness. But I always felt slightly disconnected with acts of charity.

A month ago, I went out with some friends for a few drinks. Ok, a lot of drinks. Ok, enough drinks to sedate an elephant. And I’m the kind of person that cannot go home before strolling (read: stumbling) through the doors of a local purveyor of fine, cheese-based drunk foods.

On my journey to get some pizza, I walked by a homeless person who politely asked if I had any money to spare. [Even to this day, I have mixed reactions about giving money to homeless people. On one hand, I want them to seek out the help through the proper channels and charities that exist to help them. On the other hand, those same systems often fail them. Back to the first hand, how do I know they’ll use it on something worthwhile and not on drugs? Switching hands once again, who am I to judge what they spend it on? I just spent $50 on Jameson shots alone. That ranks just above lighting money on fire in terms of usefulness.]


In this particular moment, I did not have any cash (honestly!). But out of nowhere, something clicked. I stopped, turned around, and said: “I honestly don’t have any cash. But I’m going to get pizza. If you want to come hang out and eat pizza, you’re more than welcome.” Somewhat confused but open to the idea, he agreed and came along. I asked him his name, where he was originally from, and what was his favorite kind of pizza. You know, the important stuff.


We grabbed a pizza and sat in a booth. And we just talked. I blabbered on about how I was convinced this girl at the bar liked me. We went through our favorite sports teams. And you can’t escape a drunk conversation with me before talking about music. So we talked all things Motown.


While the conversation was fun for the most part, there were some moments where we were going beyond “just talking”. I asked him how he became homeless. I asked him if he had any family. And when he saw that I genuinely wanted to understand him and his situation, with no ulterior motive or a campy “We care!” tee shirt, he started to open up. We were just two guys bullshitting.

At the end of the conversation (and pizza), I fumbled for ideas on how I could help him. And while I was mulling over a few ideas, he cut me off and said:

“You already did enough, man. It doesn’t bother me when people don’t give me any money. It bothers me when they pretend they can’t hear me. Or just straight up ignore me. The worst part about being homeless is not feeling like a human.”

And it was at that very moment when I formed my new brand of giving: Giving a damn. How do you do it? You give five minutes of your day to make someone feel special, feel important, or even in some cases… just feel like a human being.

Previous post

Veteran with Cancer Places Ad Asking for Letters

Next post

Good News from Last Week: January 30 - February 6

Patrick Gallagher

Patrick Gallagher