A few months ago I was walking home from my office and it was starting to get dark. I passed the New York Stock Exchange, and turned onto Broadway where there was a woman sitting Indian style against the side of a building. She was wearing a sweatshirt with a hood on her head. She was quiet and mostly looked toward the ground. I assumed that she was embarrassed. You could barely see her face. I guessed she might have been in her thirties, but I really only saw her for about fifteen seconds.

She had a sign in her hand. I couldn’t read it because of the handwriting. As a matter of fact, I didn’t try to.

When a homeless person is holding a sign I never read it, even though I’d often like to know what it says. Maybe it’s because I don’t want to know what happened to them. Maybe it’s because I feel guilty that their sad story is interesting to me. I always wonder how they ended up homeless. Or, maybe I feel guilty because nothing like that ever happened to me.

I continued walking for a few more blocks when I remembered something that my father had told me about one of his co-workers – a fun, selfless woman that’s nothing like me. When a homeless person or panhandler would ask her for money, she wouldn’t give it to them. She knew that many of them would just use the money for drugs or alcohol. Instead, she would buy them a meal.

Since hearing her approach I had always wanted to try this. First of all, it was an efficient way to help someone immediately. A homeless person needs a meal right away. They need to know where they’re going to sleep tonight. They can worry about tomorrow when tomorrow comes. (Read this post by James Altucher for a really great perspective on that line of thinking.) Secondly, it seemed like an adventure. The idea of a spontaneous dinner with a complete stranger was intriguing. The fact that it was a homeless stranger added a level of excitement.

By this point in my venture home I was just a few blocks from my apartment, but I decided to turn around and offer to buy the woman some food. First, I had to figure out where I was going to take her. I didn’t want her to have to walk too far. There was a McDonald’s across the street, but I didn’t want to buy her fake food. Some people would probably find it odd that I was concerned about a starving homeless person being picky – but I was. I wanted her to eat something that tasted good, was filling, and also healthy. Then I remembered that there was a sandwich place about a block away with a seating area. They had something for everyone. Even a homeless person would like their food.

I had a game plan, but now came the hard part. I had to muster up the courage to approach the woman and offer her a meal. Thinking about it now, I guess I was afraid of getting rejected by a homeless person. After watching her from across the street for a few minutes I decided to just go for it. I asked her if she was hungry. She replied that she was starving, introduced herself as Karen and proceeded to thank me. Then we began our walk to the sandwich café.

Even when not touting her sign, Karen clearly looked homeless. It felt strange to walk with her. People looked at us. I was kind of embarrassed. I felt guilty for being embarrassed. In a few minutes we arrived at the cafe. After ordering, the cashier tried to ring us up separately, assuming that we couldn’t have arrived together.

We grabbed our sandwiches and found a spot to eat. Again, I felt like people were looking at us. I was expecting Karen to eat really fast, because after all, she was starving. But she didn’t. Although, she did chew and talk with her mouth open. (Which I found funny, because I do the same thing.) It was nice to eat with someone that was honest and humble enough to not care about something like that.

She was a very pleasant person, but somewhat shy. I tried to think of things to talk about so that we could avoid awkward silences. I was reluctant to ask her about her past. I ended up giving in and asking her how she became homeless. She told me that her parents passed away when she was younger, that she was the victim of some violence and didn’t have anyone to take care of her as a child. She told me she couldn’t find an employer that would have her. I asked some follow up questions, expressed my regret and then we started talking about some lighter stuff.

As we were leaving I bought Karen one more sandwich to take on the road with her. Our time together only lasted about 45 minutes, but it was a special experience. When we got outside of the cafe to leave I told her that I had enjoyed our conversation. That’s when she said it.

“Thanks for coming to dinner with me.” And she was right. She took me out to dinner. I didn’t take her. She was the one doing the helping.

This morning I wondered if Karen was fortunate enough to eat today. I often wonder whether she found a place to sleep last night. Is she even still alive?

I have a challenge for you. The next time you see a homeless person, or someone that is hungry, offer to buy them a meal. Eat with them. If you’re in New York, you see homeless people every day. It might be different somewhere else. After you take them to eat, write me an email about your experience. I’d love to hear how it went. I’m sure everyone’s experience will be a little bit different than the next.

There are a lot of people that are homeless and hungry in New York City. I won’t have dinner with all of them, but if they have a sign, I’ll read it from now on. Who knows. Maybe tonight I’ll pretend to be homeless. Maybe tonight I’ll take someone out to dinner.

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