Tips for Engaging with Your Homeless Neighbors

January 24, 2017

It can be intimidating, walking up to someone you don’t know in a city of 8.5 million people. Especially someone whose current situation—homelessness—feels so far removed from anything you may have known or experienced. It can feel overwhelming. What do I even say? Should I just give him money and walk away? Do I offer for her to come to my apartment to clean up? Maybe I should just keep walking…

There are some 3,500+ people living on the streets of New York City at any given time. That’s not to mention the 60,000 people sleeping in city shelters each night. These people are our neighbors. And we, if we call this place home, are sent out to bring healing and restoration in the name of our God who cares deeply about the flourishing of our poor and homeless brothers and sisters (see Isaiah 58:7).

To that end, we asked three people who spend their lives engaging with our homeless neighbors for practical tips on how they do what they do. Here is a bit of the advice they offered:



They are not first and foremost homeless. They are first and foremost people who, due to some sort of trauma or difficulty, happen to be homeless. They weren't born homeless, and with the right kind of help, they will not remain homeless. They are people who grow up like us, with dreams and hopes. They can recover those.

It starts with a conversation, exchanging names, and the belief that, as much as they appear to be different than those of us who have a home, we are far more alike. Connecting with that reality humanizes them and points to solutions. Homelessness is not a problem to be solved. These people are assets of our community to be recovered.

There are dos and don'ts. Don't give money. Don't give personal information. Don't engage alone, especially with members of the opposite sex in a secluded place. I am often asked, "What should I do with the homeless person I walk by?" The short answer is:

First, offer a silent prayer. Then, introduce yourself and ask for his or her name. If you can make the time—and hopefully you can—ask if you can share a meal with them. Ask them what food they would like that's in a short walking distance. (They say beggars can't be choosers, but these people are not beggars. They are people like you who have likes and dislikes.) If they agree, then over a meal, share a bit of your story and ask for theirs. If you don't have time, bring them to the restaurant and buy it for them, or get carry out and bring it to them. Weather and their physical condition may dictate the best option.

If eating a meal together or buying one is not an option due to time or your own financial situation, and passing people who are homeless is a regular experience where you live and work and commute, then consider carrying granola bars, apples, etc. Offer them one of those items, and carry with you resource cards put out by The Rescue Alliance. Explain that this tells them where they can get help from private organizations, NOT city shelters. Many have a strong aversion to city shelters.

Finally, if they have been open and comfortable talking with you, ask if you can offer a brief prayer for them before you leave. Nine times out of 10, they will say yes.

I actually think starting out by volunteering at one of the rescue missions (New York City Rescue Mission or The Bowery Mission) can help remove misunderstandings and stereotypes. It can create ease and comfort in engaging with them, and prepare you to engage them on the street in everyday life.




  1. Don't overthink it. It's not as hard as you might imagine. Most folks who are homeless aren't engaged by anyone throughout the day.
  2. If possible, offer them a next step via our Resource Card.
  3. Put yourself in their shoes. Most homeless individuals were born into poverty, just one step or wrong decision away from the streets. See yourself in them. Ask, "What would I want the next person walking by to do or say to me?"
  4. Don't just buy them a meal (if you're going to do that). Eat with them. Buy dinner for two, if they're up for it.
  5. Some of our helping can hurt more than it helps. Attend the upcoming homeless workshop with Hope for New York, or come serve with us on a Thursday night to see how it's done well.




I am approached often by the homeless who panhandle in Penn Station or on the street. When they ask me for money, I don’t immediately respond to that request. Instead, I look them in the eye and ask their name. I introduce myself and shake their hand. This changes the paradigm immediately and changes the scenario from begging to interacting.

I ask how they are doing and where they are from. I offer to buy them something to eat, and if I have the time, I offer to eat with them. Breaking bread together, even if it’s a street hot dog, is a great way to get to know someone. While I am talking to them I try to use their name as many times as possible to reestablish their identity as human, not just homeless. After getting to know them and learning their circumstances, I offer an outreach card and explain that the people at these organizations really care and want to help. I always ask if I can pray for them. Prayer is an excellent way to have an intimate encounter with someone who is isolated and dying for human contact and love.

Something new I have done recently is offer to buy someone’s cardboard sign that they are using for begging. It changes the paradigm from begging to an exchange of goods. Begging degrades people, but selling something is honorable. The people I have bought signs from were very happy to sell them to me and we had wonderful conversations. They always let me pray for them.

I have a good friend in the corporate world who has a senior position in marketing. He purposefully goes out during his lunch hour to find a person challenged with homelessness to have lunch with. Of course, this is what New York City Relief and The Rescue Alliance does every Thursday night during our weekly Don’t Walk By outreach. It’s a great opportunity for those who are too nervous to engage with the homeless one-on-one right now, but want to help the poor. They can join a small group during this outreach, and once they find someone on the street in need, they can take them out to dinner together, break bread, and commune as equals. The more people get to know others battling homelessness, the less nervous they get. Ultimately, they discover that homeless people are just people like everyone else.