Whether it's because you feel bad for them, guilty about your privilege or simply don't know what to say, sometimes it's easier to pretend you can't see someone on the sidewalk.
Other times, we're so busy or caught up in our own lives, that we don't even see homelessness before our very eyes.
"I don't think people do it on purpose – it could be that they don't know what to say [or] it could be that we are desensitised," Major Bruce Harmer, Sydney Salvation Army Officer, tells SBS Life.
"[People] who find themselves on the street need our love, our care and attention. I've heard people say, 'If it wasn't for that person saying good morning to me today, it was going to be my last day'."
So how can you respectfully acknowledge those doing it tough without making them – or yourself – uncomfortable?
Get down on their level
There's no greater metaphorical power imbalance than looking down on somebody you are talking to.
"If I feel comfortable, I will sit down next to someone or drop on my haunches," James Toomey, Mission Australia CEO tells SBS Life.
"I just say, 'Hi I'm James', as a way of opening a conversation. It humanises you."
I've heard people say, 'If it wasn't for that person saying good morning to me today, it was going to be my last day'.
If you don't have time or feel inclined to have a conversation, Toomey says some simple eye contact can make a big difference.
"You can give a small smile – it doesn't mean you are obliged to do anything beyond that," he says.
Don't assume you know what they need
As much as you might think it helpful to hand over a sandwich or drink, it might not be what they need, so Harmer says simply asking, "Have you eaten today?" could be a good ice breaker.
"Think about what you might say before you say it," he suggests.
"Be prepared to help if they haven't had something to eat, [and] if you ask them, 'How are you?' then be ready to provide some support."
Harmer says the more you speak to people around you, the more you'll probably find yourself doing it.
"Once you have a couple of conversations, you start to have an eye for it," he says.
"You'll find yourself saying, 'How are you doing? I'm feeling thirsty – want a coffee?"
Heather Hoist, Acting CEO at Launch Housing, says it's important to remember that many homeless people don't have much privacy.
"One of the troubles with being on the street is that you can't really close the door," she says.
"So I think people have got to be sensitive [about] whether someone feels like being approached. I think [we need to be] even more respectful and polite than ever because of the lack of privacy and defences that someone has on the street."
That's where some eye contact and a smile can be a good starting point.
"Then it's the same sort of rules for striking up a conversation with any stranger," Hoist says.
"Don't assume someone hasn't thought of something [they need] or needs advice. If you think someone might want help, then ask."
If someone doesn't respond warmly to your efforts, don't hold it against them.
"Not everyone will respond – they might have had a bad day or had someone be not so nice to them around the corner," Harmer points out.
"Just back off and say, 'Sorry, I didn't meant to offend you'. Don't give up though or we will be a much lonelier society."
Reap the rewards
Speaking with people from all walks of life is not just about benefiting them. Kerry McGrath, Red Cross Director of Community Programs, says we all have much to gain from interacting with our fellow community members.
"We would learn about strength and resilience and the interesting lives that people have," she tells SBS Life.
"It's about building empathy and building an understanding connection."
Don't assume someone hasn't thought of something [they need] or needs advice. If you think someone might want help, then ask.
Harmer agrees that everyone benefits from speaking to people around them.
"You'll gain a rich understanding of these people, and you will know that you're playing a part in breaking [loneliness] down," he says.
Don't be sorry
No matter how sympathetic you feel about a person's situation, resist the urge to express your sadness.
"Avoid any questions that start with 'Why', such as, 'Why are you in this position? Why don't you get help?'" McGrath says.
"Asking, 'How can I help? What do you need?' is much more helpful."
Harmer says you should never assume somebody's life is terrible because they might not see it that way.
"We might think they are in dire straits but they might not," he says.
"Some of the folks I know on the street [in Sydney] catch a train to Nowra to sleep each night and they think their life is okay."
Know your limits
If you don't feel safe or comfortable speaking to somebody, then of course you don't have to.
"Always make sure you are not going to put yourself at risk," McGrath says.
"Try and learn about local organisations in your community so you might be able to talk to them and say, 'I've noticed this person doing it tough, I'm worried about them'."
Harmer suggests keeping Lifeline details on hand in case somebody looks like they need some support.
"If you come across somebody who is struggling, you are able to say, 'Why don't you give these people a call?'" he says.
Speaking to somebody is not the only way you can help bring more inclusiveness into our society.
"There are ways of getting involved in advocacy or campaigning, through campaigns like Everybody's Home, which is trying to create a plan to fix the national housing system so everyone has a home," Toomey says.
If this article has raised an issue for you or you/someone you know is in need of support, contact Lifeline on 13 11 14.
If you have experienced sexual assault or domestic and family violence, you can also receive counselling, information and support through 1800 RESPECT (1800 737 732).
Filthy Rich & Homeless season 2 airs over three nights starting on Tuesday 14 August 8.30pm on SBS. You can also stream the show anytime on SBS On Demand. Join the conversation with #FilthyRichHomeless.