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To make this question concrete: Let's say I am stopped at a stoplight and I see a person holding a sign asking for money.

Main question:

Am I morally obligated to help him/her?

For those who would answer yes please answer these follow-up questions.

First follow-up question, if yes:

If we are morally obligated to help the less fortunate, then does it follow that charity does not come from the heart? (Like a gift.) But, rather, charity is merely the execution of a pre-existing duty? (Like paying taxes.)

Second follow-up question, if yes:

Are we obligated to help all the poor (i.e., everyone holding a sign, etc.)? (Surely, we can't be.) Or is there a limit to the number we are obligated to help? If there is a limit, what is the number of required poor people we are required to help?

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    Related to your first followup: rabbisacks.org/…. Related to your second followup: judaism.stackexchange.com/q/52820. – msh210 Nov 13 '15 at 15:48
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    The answer is yes you are obligated to help all the poor. You have a certain minimum amount of finances that you must delegate to helping the poor. But you can decide to help some poor more than others. So for example, maybe you don't have to give food to every homeless person you see, but you could give x amount of money to your local food bank or homeless shelter – Aaron Nov 13 '15 at 18:10
  • @aaron: Thank you. Can you please point me to the clearest example of text that describes this? – Mowzer Nov 13 '15 at 18:18
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    @Mowzer The text i'm thinking of describes that you must give to any poor person that comes asking from you. But it doesn't describe the ways in which you must give. it's from Hovoth haLevavoth. Have you heard of this book? – Aaron Nov 13 '15 at 18:21
  • Possible duplicate of Jewish definition of a charity – sabbahillel Oct 18 at 11:42

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