She Gave a Homeless Young Man $20 in Downtown Portland Then Asked Him to Call His Mom After Years of Addiction and Silence

A simple act of kindness can change a life. I’m not saying my small act of kindness changed a life outright… but I truly believe it created a ripple effect, one that moved outward in a positive and meaningful way.

I was working a large event in downtown Portland, Oregon. After the first long day, my feet were sore and my body exhausted. Although I live in the Portland metro area, I stayed at a hotel that night so I could be rested and ready for Tuesday—our biggest day. Wanting to unwind, I decided to take a walk and visit my favorite shoe store, one I only get to visit every couple of years. The weather was perfect—classic Pacific Northwest fall—65 degrees, a cool breeze, and fallen leaves carpeting the sidewalks. Halfway there, I realized the store had moved, adding at least a 30-minute walk. I debated calling a Lyft or walking the two miles. My feet ached, but the city’s energy and the beauty of the evening won me over, so I kept going.

Like many large cities, Portland faces a homelessness crisis, especially downtown. I passed many people along the sidewalks, but about halfway through my walk I noticed a young man who immediately reminded me of my own son. He sat quietly with his pit bull—my favorite breed. I walked over, knelt down, and explained I didn’t have cash before asking if I could pet his dog. We talked briefly. His dog’s name was Toothless. He told me he was heading to California and hoped to someday sit on a beach with Toothless by his side.

I told him I needed to get to the store before it closed, but if he was still there on my way back, I’d stop and bring him some cash. He was incredibly sweet and tugged at my heart. Not long ago, my own son had been that young man—living on the streets, addicted, holding a sign, begging for money—while I had no idea where he was or if he was alive.

After crossing the street and rounding a corner, I immediately started searching for an ATM. An older homeless man overheard me asking for directions and kindly pointed me to an ATM just inside Powell’s Books—where I was already standing. I had about 25 minutes left before the shoe store closed. I could keep walking and buy shoes, or I could turn back. I chose the money. As I headed back to where I’d seen the young man just minutes earlier, I felt strongly that this exchange needed to mean something more. Within moments, I knew exactly what that meant.

His backpack was there, but he wasn’t. A quick scan showed him across the street talking with another young man—also homeless—with another beautiful dog. When I approached, he recognized me right away. I quietly handed him a $20 and asked, “How long has it been since you talked to your mom?” He shrugged and said it had been a long time. I asked him to do me a favor—call his mom and let her know he was alive and okay. His face lit up. He asked to borrow my phone. I hesitated for a split second, then handed it to him, trusting that God was in control and urging me forward.

He called his mom, and she answered immediately. Wanting to give them privacy, I knelt down and chatted with the other young man while petting his dog. He was older, kind, and tired. I gave him a few dollars and asked about his mom. He told me she had been on meth since before he was born, and that calling her wouldn’t matter. My heart ached for him.

Soon, the first young man told me his mom wanted me to hug him for her. He put her on speaker. The relief, joy, and emotion in her voice are hard to describe. She was confused about who I was—he explained I was just someone who stopped to help. She asked me to hug him. He protested, saying he was filthy and smelled. After he hung up, he repeated that his mom really wanted the hug—but he insisted I wouldn’t want to. I hugged him anyway. Tight. Long. Like I would my own son. A mother’s hug knows no boundaries—no stench, no addiction, no judgment. I told him I hoped he stayed sober, stayed safe, and stayed in touch with his mom.

The story didn’t end there. Two weeks later, I finally gathered the courage to call his mom. Her number was still in my phone. I secretly hoped no one would answer. Voicemail picked up, and I left a message. Less than five minutes later, my phone rang. It was a Missouri number—it was her. She and her husband were camping with limited service when she saw a missed call from Oregon and said, “Oh my gosh, did I miss a call from John?” They immediately drove to higher ground for reception. She was near tears when she realized I was the woman who had asked her son to call.

We spoke briefly, but long enough to recognize each other as kindred spirits—mothers walking the same road. She hadn’t heard from her son in five weeks and wasn’t sure he was alive. She had been praying for his call. I had been the answer. She asked if she could call me again when she returned home. I know now I’ve gained another sister, another lifeline.

That night, I shared a shorter version of this story on Facebook, hoping to raise awareness and encourage kindness—to look beyond the signs, the smell, the struggle, and see the human face. One comment read, “Tonight you hugged all of our struggling sons.”

My message to you is simple: hug someone’s struggling son or daughter. Listen to that inner voice. Look deeper. Love freely.

PS: I ordered my shoes online that night.

Leave a Comment