Do you have a dumb question that you're kind of embarrassed to ask in the main thread? Is there something you're just not sure about?
This is your opportunity to ask questions. No question too simple or too silly.
Culture war topics are accepted, and proposals for a better intro post are appreciated.
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Notes -
If that is a question that you really want to know the answer to then ask a police officer that is stationed in area. They are the ones that enforce the rules/laws so they should be able to give you an idea of how this would play out and may give you some tips on how to do it in a way that would cause the least amount of trouble for you. They probably dislike dealing with the hobos so they might be incentivized to give you useful advice in dealing with the situation. The caveat being that an individual police officer may not speak for the whole department.
I think a more relevant question is:
The answer to that question is probably close to never, unless you are personally in danger and can't deescalate the situation in some other way.
Hobos have a lot less to lose than you. A sad reality, as you are probably aware, is that many times the person who cares the least about the consequences of their actions often has a power advantage in the situation. Gabbling hobos usually fall into at least one of 2 general buckets:
Furthermore, this question has an ethical component:
My personal view on this is something like this: If society encourages/rewards me for helping people, and there is no risk of consequences to me, then I will often be happy to help other people. To a limit of course: I'm not being paid to do it and therefore much of my time needs to be spent pursuing my own economic interests. There are many benefits to society (and therefore me as participant in said society) if people help each other out, and doing good deeds can often be its own reward.
However, in your story so mention your coworker's attitude to this situation was to worry about that "that poor man's mental illness" instead of encouraging you to help the woman. Ideally, society's response to standing up to hobos that are harassing people would be something like this:
If those conditions are not all met then my default response would be that I'm only responsible and obligated to solve problems that personally impact me. If there is a problem in society where those conditions are not met then other people need to change their norms and attitudes to incentivize me to help them.
If society wants to tolerate anti-social behaviors in an attempt to be more compassionate towards people suffering mental health issues then that is fine. Just don't expect people to be good Samaritans when that "tolerance" creates social stigma against intervening in situations where someone with mental health issues is causing problems for others.
I'll find other situations and environments where my help is appreciated and respected.
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