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I used to work in Downtown Orlando, which is notorious for its amount of people walking the streets no matter if it's day or night. I worked Downtown for about six months, and I started to notice the people who were peddling every day, as well as people who were truly homeless sleeping outside my office building. After a while, it started to get uncomfortable walking around town on my breaks or time off. It got to a point where I couldn't even use headphones because I had to listen to the environment around me.

Here is some clarity into one situation I was in:

In one situation, a person stood right in the exit of the parking lot (one way in/out) and wouldn't move until I answered him (he was asking for money). I couldn't drive away until he moved out of the way, and I didn't want to make a big deal out of anything.

Also,
I am not saying one should treat the homeless in a different manner - and I find it very keen to listen to what's around me, otherwise, you're going to get hurt or something pickpocketed from you.

What is the best way to handle a difficult encounter with someone who is truly homeless - and also other situations with people who aren't homeless?

closed as off-topic by Sagar VD, Joe S, Rand al'Thor, Tim, curiousdannii Jun 28 '17 at 7:05

This question appears to be off-topic. The users who voted to close gave this specific reason:

  • "This question does not appear to be about interpersonal skills, within the scope defined in the help center." – Sagar VD, Joe S, Tim, curiousdannii
If this question can be reworded to fit the rules in the help center, please edit the question.

  • "How can I tell the difference between beggars and the homeless?" is a bit off topic, as it's not really about interpersonal skills. – LMGagne Jun 27 '17 at 17:51
  • I think it is if they are in your space and there are situations where you can't simply walk away - and if it happens a lot... especially in cities. – Robert Dewitt Jun 27 '17 at 17:54
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    The bit about how to handle an encounter with a beggar/homeless person is good, but I was referring specifically the bit about telling the difference. – LMGagne Jun 27 '17 at 17:57
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    I don't understand what you're asking. What sort of "difficult encounter"? Why does someone being a beggar or a homeless person mean you should treat them any differently from anyone else? Why did you have to listen to the environment around you, and what does that have to do with beggars or homeless people? – Rand al'Thor Jun 27 '17 at 18:07
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    Are you specifically asking how to refuse a request for money, or do you have a general problem interacting with homeless people? – Gregory Avery-Weir Jun 27 '17 at 18:22
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If they're people that you see on a regular basis, and keep in mind that they're still people, try to set boundaries that you're comfortable with like you would with anyone else.

I've​ had some practice working at a local food pantry and soup kitchen. Most people who are homeless aren't bad people, they've just had rough lives. If you can extend a little humanity they'll tend to respond in kind.

Simple things like remembering names, or asking how their day was can go a long way towards making interactions a little more natural.

There's a tendency for people to develop an us vs them mentality in these situations because believe it or not both parties are often feeling uncomfortable and suspicious. The person asking for food or money usually doesn't like doing it anymore than you like hearing it.

But as I said before if you can extend a little humanity, remember a name, and be kind for a moment, you'll probably start to see them as your neighbors, maybe even as friends and they'll start to see you that way as well. Once a neighborly relationship has formed a lot of issues simply aren't issues anymore. You may even find that they stick up for you when hustlers give you trouble or other people aren't being respectful of your property.

Obviously, like in any interpersonal relationship, boundaries are important. If you don't have anything to share on a particular day don't be afraid to say so, but still remember that you're talking to a person, be assertive, but be kind. In my experience taking a moment to get to know people makes this easier and they'll respond much better as well.

To use the specific situation in your question...

Chances are pretty good that this person is desperate and has been ignored by most of society for a while and so they're lashing out. Take a moment to imagine how it feels when you're hungry and most people won't even look at you.

In this specific instance I would probably offer them a dollar or two, take a moment to chat, ask their name and so on, but also gently tell them that while I understand their frustration, most people would probably have called the police. It's kind of a nicer way to say "I'll help you out this time, but don't do this again."

  • "In this specific instance I would probably offer them a dollar or two, take a moment to chat, ask their name and so on, but also gently tell them that while I understand their frustration, most people would probably have called the police. It's kind of a nicer way to say "I'll help you out this time, but don't do this again." - Word! – Casebash Jun 29 '17 at 1:17
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It may not have to be difficult.

If you were homeless and forced to ask for assistance, how would you want to be treated by someone walking by. Answer the question for yourself.

Based on that answer, now answer the question of what you can do (if anything) to help this person when you are the guy that is walking by. If you have an honest answer to this question, then it is no longer "difficult". Do what you can consistent with the answer you come up with.

As for the regular peddlers who are not actually homeless, have an answer for that too: ignore it, simply move on, give him advice, whatever. But do not confuse this person with someone who is down on his luck and desperately needs a helping hand.

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