I think the main point is to show him that he can watch films, listen to music, go to a bar and still remain a 100% religious jew. Enjoying life in these ways is NOT mutually exclusive to judaism. Don’t let him think that either he keeps the charedi ideology or he may as well break shabbat. As if it was all or nothing. Give him the opportunity to do both, and then, when he is older and understands more the reasons why charedim have these chumras, he can choose for himself if he wants to accept them. But either way, he will remain 100% religious.
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