7 Kind Things to Say to the Homeless When You Feel Awkward

Very often, when we see homeless people, we are often confronted with a whole lot of uncomfortable emotions that we don’t want to feel. We might feel sympathy, anger (if we were sincere), fear for our financial security, we might feel guilty about our positions, or we may feel awkward about not knowing what to say or how to act.

As dreadful as it sounds, sometimes it’s easier to pretend you can’t see homelessness. Other times, we’re so busy or caught up in our own lives that we don’t even know the situation right in front of us. You might sense aggression or frustration from homeless people; the problem is, the more frustrated we feel, the more people want to stay away from us. It’s a catch 22.

Many of us deliberately shut out the strains and pressures of others, and while it doesn’t sound great, people are wired to focus on their survival. What we have to remember is that were are all humans with a need to be seen and valued as people; being ignored continuously is a catastrophic and dehumanizing experience.

Don’t get us wrong; it would be wholly unrealistic to expect individual people to try and right all of the world’s wrongs, but think; what could be achieved if every one of us displayed micro acts of kindness every day?

In this case, an act of kindness could be as small as a smile or a quick chat with someone who is down on their luck. If you are in a situation where you’re having a conversation with a homeless person, what do you say? You don’t have to state the obvious, and we have a few better suggestions.

Template 1 | Offer Hospitality


Can I get you anything?

Seeing somebody struggling on the streets can be absolutely heart-wrenching. You might not know their story or how they got to where they are, but you can still relate to them on a personal level.

At the end of the day, even though they might not be in an ideal situation, homeless people are PEOPLE – a fact that too many people seem to overlook.

You don’t need to offer cash to help the homeless. You may wish to buy them food if they look hungry or a hot coffee on a cold day.

By simply asking if you can get them anything, you’re making them feel human again. You’re reminding him/her that there are caring people in the world, and you genuinely only want to help – even if that’s only by a small gesture.

Don’t assume that somebody who is homeless will want you to buy them a sandwich or a drink; it’s better to ask them in order to gauge a response.

Template 2 | Don’t Feel Pressured To Give Change


I don’t carry cash – is there another way I can help you?

The hard truth is that many people don’t like to give their spare change to the homeless. This could be for a multitude of reasons, though it’s common for people to believe that people who are homeless will only spend the cash on alcohol or drugs. Others may genuinely just not carry cash.

This script is very similar to the last one, only instead of offering to physically get something, be it food or a drink, you’re asking if there is any way you can help. Somebody who is homeless may not know the city too well, especially if they’ve only just arrived, so may benefit from directions.

They may ask you where the nearest hostel or restaurant is, or if they can make a phone call – how you help is entirely up to you. It’s important to remember that you should only ever act on things that you are comfortable doing.

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Template 3 | Talk To Them


How are you doing?

A simple conversation can go a long way. Homeless people are overlooked by most people who pass them, which can be a demoralizing or dehumanizing experience.

You should endeavor to just talk to them as if they were a friend or acquaintance. Those who are homeless generally express loneliness, and a casual conversation can help to brighten their day, even if only for a few minutes.

Template 4 | Sit down next to them (but only if you feel comfortable enough to do so)


Hey, did you catch the game?

This one isn’t so much something that you can say; it’s more of how you can act. Someone who is homeless might be propped against a door or sat on the floor, meaning that many passers-by will talk to them by looking down on them.

Looking down on someone as you talk can be intimidating and rude, so if you do choose to speak to someone who is down on their luck, you should adhere to do it at their own level.

Don’t sit next to them if you feel uncomfortable doing so – you absolutely need to prioritize your own wellbeing first.

If you do choose to sit down next to a homeless person as you speak to them, you can improve their mood or prompt them to be more responsive.

Template 5 | A Friendly Greeting


Good morning
Good afternoon

You don’t need to have a lengthy conversation – sometimes, a friendly greeting can be enough to drastically improve their day.

Say hello as you would to anyone else; it’s one of the best ways to casually interact with someone. A simple greeting can help to remind a homeless man or woman that they are really no different from anyone else – they’re just in a different situation.

Even if you see the same person every day, you should always say good morning or good afternoon. It might help them to realize that you actually care, and your actions will not go unnoticed. Why not try bringing them a coffee every once in a while? The relationship will help you to provide hope which they may otherwise not have.

Template 6 | Wish Them Well


Good luck with the future!

If you do happen to have a chat with a homeless person, you don’t need to leave it awkwardly. There’s absolutely nothing wrong to wish them luck for the future, especially if you know you won’t see them for a long time.

Homeless people are not any different from anyone else, so you shouldn’t treat them as if they were. If you’d wish a friend or family member that you don’t see too often a successful future, you should try to do the same to the homeless.

It’s a polite interaction, and you never know: your words might inspire them!

Template 7 | Ask About Their Pet


He’s lovely! What breed is he? Do you mind if I pet him?

Many homeless people that you come across will be accompanied by a trusty pet; sometimes it’s a friendly pup that loves to say hello, other times it’s a weather-worn old boy who’s content to watch the world fly by.

If you notice a homeless person has a pet, it could be a great way to strike up a conversation. You may want to ask if you can pet their companion, or just about their story. Either way, most people will be more than happy to tell you about their furry friend.

Don’t be put off if they say no, as not everyone likes to show their animal off. It might even be wary of people. You should use the opportunity to ask about their day, or to offer help in some way.

If a homeless person is accompanied by a pet, why not ask them if you can bring them some pet food or some old bedding that you no longer use?

At Never the Right Word, our aim is to give you practical examples of how to handle life’s difficult conversations. If you have an awkward situation that you’d like example templates for, request a topic here.  

If you’re interested in further reading, we’ve also included links to our trusted resources and related posts below. To find out more about NTRW and our recommended tools, you can do that here.

Lastly, if you found this content helpful or want to share your own examples, let us know in the comments. We’d also be delighted if you shared this article and joined us on social media too!

Article by Never the Right Word

Scripts & Templates for Life’s Uncomfortable Conversations. Learn more about NTRW here. NTRW is supported by adverts and affiliate marketing links. For more info, please see our Earnings Disclosure.

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Never the Right Word

Never the Right Word

Hi there! I’m Amy, and I’m the person behind Never the Right Word. I’m a designer-by-day who’s fascinated by human psychology; you’ll find me learning about what makes others tick through all types of media and good old-fashioned conversation. Learn more about me here.

In 2019 Never the Right Word was born to fill the gap of ‘how-to’ websites with copy and paste examples showing you EXACTLY what you need to say to steer difficult conversations into positive outcomes.

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