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but I’m wondering what the Torah position is when we think about it rationally, leaving our emotions aside.
Why would we cast aside our emotions when we are dealing with an emotional question?
Precisely because it is an emotional question, you have to put emotion aside. There is no way to objectively solve a moral dilemma when your emotions are pushing you to a biased decision, and you will just rationalize what you feel is correct without even realizing that the voice isn’t one of reason. You’ve got to put all personal נגיעות out the window, and think about it properly. Only then can you rely that your decision has been thought out.
@yes-its-me: we have yet to find a functional OTD kid
I think you underestimate the allure of the Big Bad Beyond and the social power of bad friends. Sadly, not every child who is OTD is “non functional”. I have met too many OTD people who are the only too sane. It’s called the יצר הרע.