Five Things to Say to a Person Who’s Homeless

5 things to say

Advice for the tongue-tied

So, you’ve taken my advice and stopped ignoring the homeless people you meet. But you may have found that stopping this anti-social behavior can sometimes lead to more interaction. Now, if you’re not a natural conversationalist (I, for one, am the type to accidentally say “you too” when a waitress tells me to enjoy my meal) you may find yourself at a loss for words.

Speaking to someone with a vastly different perspective than yours is always especially fraught. You don’t want to say the wrong thing and inadvertently upset or offend them! But you shouldn’t build up “talking to a homeless person” in your mind as something that’s vastly different from talking to any other kind of person. Thoughts like that aren’t based in reality, and they’ll only make you more nervous!

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.

If you’re not able to give cash, just be honest by saying something like, “I don’t have any cash, but is there another way I can help you?” 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.

If you’re not much of a sports person, test the waters with other big televised events. Or take your cue from them by asking what they’ve seen lately.

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.

Don’t be surprised if you get a “fine” or “as good as can be” for an answer. Even though you might think things can’t possibly be going fine for this person, they probably just don’t want to share their life story and inner thoughts and feelings with a complete stranger right off the bat.

If they give a negative answer, though, you could follow up with something like, “would you like to talk about that?” Now suddenly you’ve gone from exchanging simple pleasantries to really getting to know someone.

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.

Just be a little bit careful with this one. If it’s the only thing you say to a person, or your words aren’t backed up by concrete actions, it can sound a bit like, “thoughts and prayers.”

It’s always best to couple your well wishes with something that actually helps in the moment. But once you’ve done that, a parting wish of goodwill like this one can be the icing on the cake.

Just like icing, it’s not that great on its own.

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!

Of course, for it to take you anywhere, you’re going to need to actually use these conversation starters in real life. So, get out of your own head, into your city, and start broadening your horizons. No doubt you’ve seen some of the amazing interviews with people who are homeless featured on this site. But truth be told, there are people like that just about everywhere, often going unnoticed.

Kayla Robbins

Kayla Robbins


Kayla Robbins is a freelance writer who works with big-hearted brands and businesses. When she's not working, she enjoys knitting socks, rolling d20s, and binging episodes of The Great British Bake Off.

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