How Do You “Encounter” a Person Who Is Homeless?

by | Dec 15, 2022 | Formation, Homelessness, Reflections

Pope Francis constantly stresses we should encounter one another. So many of our conversations remain at a surface level.

But let me go a step further. When was the last time you spoke with a homeless person… The first step to any encounter?

I don’t mean simply noticing one as you pass by. I know from personal experience how easy it is to walk by, seeing but not seeing a homeless person.

Speaking to someone living in vastly different circumstances than you are in seems to be much trickier. Where do you start?

Kayla Robbins, writing for “Invisible People,” offers some very simple ways of approaching a homeless person.

It is actually not much different from speaking with anyone else.

From a simple “hello” to a “what do you need today?”, there are many things you can say to try and connect with a homeless person you meet, however much or little you want to engage at that moment.

These 5 things to say will move things along until you get into the natural flow of conversation.


Hi, hey, hi there, good morning, or even howdy are all no-brainers when it comes to greetings. They’re multipurpose as either a great way to start off any conversation or a pleasantry to exchange in passing. Most of the time, this is all you’ll need to say.

You have this interaction multiple times per day. You make eye contact with someone, smile, exchange a greeting, maybe a few pleasantries if you’re taking the same elevator or something. Then you each go about your days. It’s no different when it happens with a person who happens to be homeless.

How Can I Help You Today?

If you want to help a homeless person you meet, try asking first if they need assistance. If so, what. It’s always better to ask what’s needed than to assume or hand out pre-made, one-size-fits-all kits. It’s not a bad idea to keep commonly asked for items on hand. But keep in mind that one size definitely does not fit all.

” You may be surprised by the answers you get. Sometimes food, clothing, information, transportation, or just someone to talk with are what’s needed most at that moment.

Did You See the Game Last Night?

Sports are a great way to bring people from all backgrounds together for a common cause. Big sporting events are also often shown in shelters and other public places. So, there’s a decent chance the person you’re talking to saw it if they wanted to.

Talking about sports is a nice way to pass a few minutes for anyone. For a homeless person, in particular, it can get their mind off the everyday difficulties of being homeless and make them feel “normal” again.

How Are You Doing?

Asking how a person is doing and genuinely wanting to hear the answer is a powerful tool for connection between any two people. Asking this question of a homeless person you meet gives them the opportunity to answer as they wish … either with a heartfelt response or by shrugging off the question.

Open-ended questions like these are good because they give the person you’re talking to full control over how deep the conversation goes.

I’ll Be Thinking of You

For some people, it can be comforting to know that someone out there is thinking of them, praying for them, or sending them good vibes. Particularly with homeless people who are religious, praying for or with them is a meaningful gift.

If you’ve been able to connect with the person you’re talking to and really start getting to know them, this can be an especially powerful way to sign off your conversation with them.

Now Go and Use Them!

There you have it, 5 useful and easy to remember conversation starters to use any time you’re caught in an unexpected social situation. When making eye contact and smiling doesn’t feel like enough, use one of these ideas to start forming a more meaningful connection with someone. You never know where the conversation may take you!

Kayla Robbins

Kayla Robbins is a freelance writer who works with big-hearted brands and businesses. The excerots originally appeared on | August 15, 2019