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If, on Purim, "Reuvein" asks "Shimon" if the latter knows the difference between Haman and Mordechai may Shimon lie and answer 'No'?

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Yes! According to the Maharsha in his chiddushei aggadot on talmud bava metzia (s.v. b'puryah). CF Titen Emes L’Yaakov page 52:26. Moadim V’zemanim (Rav Moshe Shternbuch shlitah) 6:109 who explains this opinion.

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Why would he be allowed to lie? –  Double AA Mar 13 at 16:58
    
@DoubleAA that is an interesting question which is worth asking. Ayin the sources I quote for more information. –  user5092 Mar 13 at 17:08
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That question is this question. Including your reasoning will improve the value of your answer. –  Double AA Mar 13 at 17:09
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If indeed we follow the Maharsha's explanation of the Gemara, does that mean to the exclusion of all of the other rishonim who explain that gemara to be referring to something else entirely? If so it's hard to imagine why we should pasken like that. (On the other hand, even without the Maharsha the answer may still be yes, as otherwise "Reuvain" might pressure or argue "Shimon" into drinking more, which could cause a fight or 'perikas ol', as R' Moshe Shternbach mentions.) –  Matt Mar 13 at 20:26
    
@DoubleAA I disagree. A question such as may one cook milk and meat together if very different from the theological question of why the torah proscribes it. –  user5092 Mar 14 at 13:21
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