Last week I wrote about why homelessness makes us so uncomfortable, telling a story of how I failed a homeless man in Chicago while my fiancée, Alexis, and I were celebrating our fifth dating anniversary. This week I'd like to tell you a very different sort of story from an encounter that happened just two days later.
It was a Saturday, and we had come to spend an entire day in the city, this time with no specific plans other than to use our two Willis Tower Skydeck tickets. We decided to knock that out first so we could spend the rest of the day walking around enjoying the city.
After getting the touristy excursion out of our system, we headed down Jackson toward Millenium Park because that's just what you do when you're not from the city and don't have plans. As we reached Michigan Avenue and prepared to cross over to the front steps of the Art Institute, I noticed a homeless man with a cat on the corner.
As usual, Alexis and I just walked on by. But this time, something was different.
We crossed the street and sat down with a small crowd on the steps of the Art Institute to enjoy some street performers, but I found myself distracted by the homeless man who I could still see across the street.
Maybe it was because our experience from two days prior was still fresh on my mind, or maybe it was a prompting from the Holy Spirit—a divine nudge of sorts. It was probably both. Either way, I felt like we needed to go back and engage with that man and his cat somehow. So we did.
We got up and circled back around the block, and as we came down the street toward the man with the cat, Alexis said what we were both thinking, "This is uncomfortable."
"Yes, it is," I said. "Just follow my lead."
Bold words from someone who was just as uncertain about this whole thing as she was.
The man with the cat was sitting just outside the doors of a Walgreens. When we finally got there, we shook hands and introduced ourselves.
"I'm Jason, and this is Merlin," he said, pointing to the cat who was wearing a thin sweater and enjoying a recently-donated can of cat food.
"Nice to meet you, Jason. Is there anything we can get you from the Walgreens right here?" I asked, still very uncertain about the whole thing.
"Well, some chocolate chip granola bars and maybe a Pepsi would be nice," he replied. "And maybe a small blanket to help Merlin here keep warm at night if you can find one that isn't too expensive. All he's got is that sweater he's wearing, and I only have one blanket myself."
"I think we can do that," I said. "We'll be right back."
After we had collected the granola bars and Pepsi inside, we searched for something that could be used as a blanket for Merlin, but no such luck.
As we headed toward the cashier, Alexis stopped me and said, "I don't agree with this."
Perplexed, I paused for a moment to figure out what she meant before replying, "With what? With just giving the man a handout and walking away again to move on with our lives?"
"Yes," she said.
Suddenly enlightened, I replied, "Now that you mention it, I don't either."
We ended up sitting down on the sidewalk with Jason for a good half-hour or so, just asking questions and listening to what he had to say. The sun was beginning to set, and it was a bit chilly, so Merlin sat curled up in my lap the whole time. I wish we had found him a blanket.
During our short time with Jason, we got to hear his story and learn about what it was like to live on the streets. And, wow, did I have a lot to learn. I would never have realized how hard it was to actually get back on your feet in a situation like his. But more on that in Part Two next week.
Instead of just giving Jason a handout and moving on with our lives, we stopped to engage with him. We dove headfirst into discomfort, instead of merely brushing shoulders with it, and I'm so glad we did. We got to do more than just meet a physical need; we got to connect with a man who otherwise felt pretty much alone.
I left far more brokenhearted than I had been coming into that conversation, but I'm starting to learn a broken heart is a lot better than a hardened one.
I may not have changed much for him, but that encounter definitely changed something in me.




















