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Woman Gives Homeless Stranger Her Boots in Freezing Chicago and Walks Home in Stranger’s “Old” Pair

Woman Gives Homeless Stranger Her Boots in Freezing Chicago and Walks Home in Stranger’s “Old” Pair

I went to the Chicago Bears game today. By the time the day was over, we had spent $32 on train fares, $200 on tickets, $7 on a hotdog, and another $41 at Giordanos. We paid all that just to have a fun day in the city, even though it was freezing. And honestly, I feel guilty about it. We have more than enough, and at the same time, nothing close to what so many other people have. It is a strange feeling to carry.

The high was only 30 degrees, so I was bundled up like I was heading into a blizzard: Under Armor pants and a long sleeve, two more pairs of pants, four shirts, two sweatshirts, three pairs of socks, two pairs of gloves, a coat, hat, scarf, and my favorite new winter boots. Inside Giordanos I warmed up so much that I stripped down to just my Under Armor shirt, pants, socks, boots, and hat. Everything else I stuffed into a bag. When we left, I just put my coat back on and carried the bag with me.

We were walking to the train when I saw her, a homeless woman crouched down on the corner trying to keep warm. The walk signal turned on, and the four of us rushed across the street so we would not miss the train. But the second I got to the other side, my stomach dropped. I felt sick. I had passed so many homeless people that day, but something about her pulled at me. I asked everyone to give me a minute and I ran back across the street.

As I got closer, I noticed her cardboard sign.
“I am in need of winter boots and winter clothing items.”

It stopped me cold. Because in that bag I was holding, I had exactly that. And the boots she was wearing were soaked and falling apart. Mine were warm, waterproof, practically new. At that moment, I knew exactly what I was supposed to do.

I asked her what size boots she wore. “Eight and a half,” she said. Same as me.
What size shirt? “Medium.” Same as me.

I honestly felt a little crazy, because I knew I was about to walk through Chicago winter in just my socks, but I also knew that this was not a coincidence.

I handed her the whole bag of clothes from Giordanos, shirts, sweatshirts, gloves, scarves, plus my leftover pizza. Then I told her I wanted to give her my boots.

She stood up and started crying.

I sat down on the curb with her, untied my boots, and even pulled off the top layer of my warm fuzzy socks to give her. She told me they were the nicest shoes she had ever had.

Her name was Amy. We exchanged just a few words, but honestly, most of what we said was not verbal. When I first saw her, her eyes looked tired and worn down. By the time I left, there was this softness in her face, a warmth that I had not seen before. Gratitude, maybe. Or relief. Something real.

As I started to leave, she called out, “I do not want your feet to be cold. Can I give you my old boots?”

She had almost nothing, and still offered me her boots.
So I wore them all the way home.

I cannot stop thinking about her.

If you ever feel even a small nudge to do something kind for someone, follow it. It matters more than you think.

Credit: Kelly McGuire