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As a hypothetical example suppose I have a non-orthodox relative, say an Aunt. I see this relative infrequently, say at family functions 3-4 times a year. Each time I see this relative I make overtures to my Aunt about becoming more religious. She has made it abundantly clear that she is not interested, will never be interested, and finds it slightly harassing that I continue to bring it up.

At what point, if any, can a person give up on trying to encourage a non-religious person to become more religious?

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Directly pushing is but one way of doing kiruv. Are you asking "when do I stop nagging" or "when do I stop trying anything"? (And what else have you tried?) – Monica Cellio Feb 10 '14 at 22:48
@MonicaCellio trying anything. The above example was fictitious. – please remove my account Feb 11 '14 at 14:33
What is the "obligation of kiruv"? There is an obligation of tochecha, but it seems likely that one was exempt from the outset in your scenario since there is basically no chance it would be heeded. There is, it would seem, a mitzvah to bring others close to Hashem but any illusion that the manner described would effectively do so was shattered long ago in the example. – Yirmeyahu Feb 11 '14 at 16:15

a friend of mine asked the famous Rabbi Shteinman about kiruv and he replied, "don't debate with them (to convince them), just learn torah with them". i.e. try to raise them up spiritually so they will have the strength to see the truth. debating or even worse nagging will not accomplish anything except make them upset with you as you can see first hand.

If you can't learn with them or take them to shabbatons or the like, of spiritually uplifting things, then there's not much else you can do.

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I assume the last sentence is your own extrapolation from Rabbi Shteinman's statement. Can you source that idea? – please remove my account Feb 11 '14 at 14:35
@pleaseremovemyaccount just my extrapolation. not saying to give up finding ways to uplift them, just that logically debating with them is useless, as i have seen from personal experience. they are unable to change. see this dafyomireview.com/article.php?docid=391#ch3_14 analogy about the spider. I once heard from Rabbi Mendel Weinbach zt'l the rosh yeshiva of ohr somayach that the primary ingredient of his success is due to taking the baalei teshuvas out of their secular environment and incubate them into a torah environment. without this, he said, the tayvas, block and beck at them – ray Feb 11 '14 at 18:13
harav shach was once asked which one mitzvah should one encourage a chiloni to start with. he said kashrus. He later explained that all the while that a person is eating treif his head is thick as a plank and no sense can get in, if he starts eating kosher, his brain will clear, and he will see the truth!! – rabbi Feb 12 '14 at 22:55

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