About a year ago, a friend was sitting at a light in Baltimore where some ‘squeegee kids’ were washing car windows and collecting tips. It’s not as common as intersection cardboard sign panhandling, but it’s pretty prevalent. And, naturally, there is some angst about it.

After her windshield was cleaned, she wanted to encourage the kids’ entrepreneur-ism and industriousness. She opened her window and pulled her purse into her lap, rooting around for some spare change.
But she never had a chance to find any. In a flash, a boy snatched the purse from her, disappearing into an alley. Dazed, she watched the light turn green, but couldn’t move forward. The car behind her blasted its horn.
Sidewalk Rescue
Fast forward to this past summer. My wife Nora and I were at Artscape – Baltimore’s huge outdoor arts festival – to see Grey pound on his bass drum.
We had come from different directions, so had two cars. After the performance, we went our separate ways. My trip home was uneventful; Nora’s wasn’t.
Driving up Calvert Street, she just happened to see an elderly woman trip and fall on the sidewalk. Nora quickly pulled over and ran to her side. She had a couple wadded tissues in her purse that she used to staunch the woman’s bleeding hand.
How did she feel? Where did she live? Before long, Nora dropped her off at her senior living facility, into the hands of staff there. It wasn’t exactly a Good Samaritan moment, but Nora felt fortunate that she had seen the fall, and satisfied that she could help.
Loitering Youths
A few months later, I was pouring wine at an inner city fundraiser. Pippa’s school was hosting its annual Wine Tasting and I was volunteering as a member of the Father’s Club.
I finished my bar-tending shift and descended the school’s historic slate stairs. It was cold and dark outside.
In the school lobby, I paused to put on my coat. I waved to the security guy there. “Where you headed?” he asked.
“The corner,” I pointed. It was half a block away.

“There are five youths loitering at that corner,” he said with a stern look, gesturing toward his bank of monitors. “I recommend you wait here for now.”
“Nah, I’m going to head out. You keep an eye on me and come rescue me if I need it,” I responded. I had a plate full of sweets I’d pinched from the party that I could always distribute if things got tense, I figured. đ
The security guy’s self-seriousness was totally over the top, but he was probably right to worry somewhat. By most any measure, Baltimore is a dangerous city. It has more than its share of poverty, drug addiction, gangs, and crime.
How to Respond?
How should we respond to menacing or needy people on the street? Should we engage? How?
Overall, I think engagement is good. It affirms the basic dignity of people, all of whom are created in God’s image.
There are limits, of course. I withhold my affirming in certain neighborhoods late at night, for example. My mom says “Nothing good happens in the city after midnight.” That’s a gross over-generalization, but there’s a kernel of truth in it.
I don’t generally give cash, because it’s hard to know where the money goes, and there is some vulnerability in the exchange. Rather, I donate to places like Helping Up Mission, a Christian addiction treatment and homeless shelter.
And I like to donate food, which is usually happily received. The doggy bag from a restaurant, or grocery items in the Safeway parking lot.
I know some people who won’t even cross into the city. In a car even. “It’s too dangerous,” they say.
It is dangerous, but life is dangerous. Every year in the U.S.:
- 40,100 people die in car accidents
- 5,984 pedestrians are struck and killed
- 335 people die by drowning in a bathtub
Everyone who has ever lived has died or will die. Life is a death sentence. It’s only by the grace of God that we wake up every morning.
Surprise Email
Just recently, Nora received an unexpected email at her school:
Dear Nora,
This is a very belated note to thank you for stopping on Calvert Street in July in order to see if I needed help after I had fallen on the sidewalk. You were so kind to pick me up and then to drive me home to [my care facility]. I have told many people of your thoughtfulness, but I wasnât sure how to get in touch with you. This problem was solved a few days ago when I talked to the daughter of [friends] who are residents here. I knew that her son had gone to [your school] and I thought that she would know you. I was right and she gave me your address.
I shall always remember your kindness. It actually took my mind away from my injuries – broken but not badly wrist and some loosened teeth. I have recovered well and my memory of tripping has more or less vanished while your calmness and helpfulness remain. Many thanks again.
After that email, I’m sure Nora will continue to engage with people on the street.
I will too.
Have you had any positive or negative encounters with strangers on the street?
Related: My Jury Experience Opened My Eyes to a Broken Baltimore
I give food on the streets at home and when I’m on holiday in the States to people who are clearly homeless. However there are lots of organised gangs begging so you have to be careful. I also give to shelters as you know it goes to the real needy.
It’s hard to know how to help sometimes, but shelter support seems like a no brainer
I deleted the “Street Attack” section of this post – the wife who was reported to be murdered by a panhandler, was actually killed by her husband and step-daughter, according to police. https://www.baltimoresun.com/news/maryland/crime/bs-md-ci-jacquelyn-smith-update-20190303-story.html A pretty outrageous crime.
If the person speaks to me, I speak to them. In other words, I never initiate conversation but I also never act as if the person is invisible if they address me. I never give cash because I don’t know where the money is going. In general, I don’t have food on me so I rarely have any to give. I have been verbally accosted and by the strict legal definition, I have been assaulted although that seems like an exaggeration when the specifics are recounted. I won’t be browbeaten or hectored. I usually respond to that kind of behavior by walking away.
The vast majority of the chronic homeless are addicted to drugs and/or alcohol or are mentally unstable. For you own safety, you should be wary around these individuals.
I consider myself ill-equipped and ill-suited to helping homeless people directly. I have to admit there is an element of disgust and revulsion as well as fear. The homeless can be dangerous but they are also smelly, dirty, unhygienic and a sad commentary on society. These are aspects of life I would just as soon avoid. I cut checks to various charities and am done with it as far as my conscience goes.
It’s hard, for sure. Personally, I take feelings of discomfort as a sign that maybe I’m stepping out a bit and making a difference.
Sounds as though you are doing it as much for yourself as the homeless.
My contempt is absolute for people who volunteer to feed the homeless on Thanksgiving Day (for some it has to be Thanksgiving Day and no other day of the year) and then do nothing else for the homeless for the rest of the year. I’m not saying this describes you but I question how your personal interactions with the homeless help them compared to a cash donation (or volunteering your time) to a charity that feeds/houses/treats the homeless. Homeless people get to eat well on Thanksgiving Day. That’s great but what about the other 364 days of the year? Homeless people get their basic dignity affirmed through their interactions with you but I suspect most don’t value the interaction for long as the pressing problems of their lives quickly reappear.
My vision of engagement includes more than friendly conversation đ It’s volunteering and check-writing. And although Thanksgiving-only volunteering is sort of lame, it’s better than nothing. And in some respects, it’s better than hiding behind a checkbook, like some people do. Pushing past fear and discomfort and getting out there often has a profound impact on the volunteer.