According to Halacha, is it permissible for a man to listen to a woman and man (or multiple men and women) singing at the same time, on the principle the men’s voice would override kol Isha? Or would it be kol Isha inherently?

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This is a classical question as it applies to singing zemirot (Shabbat songs) together between men and women. There is a famous teshuva from the Sridei Eish on the topic (see here on MY), showing there are sources to be lenient but many oppose mixed singing.

The best summary of the issue I found is by R Chaim Jachter here - but see the original (sub-title Zemirot) for the full text

R Yechiel Yaakov Weinberg (Teshuvot Seridei Eish 2:8) notes that traditionally women refrained from singing Zemirot when there were males who were not family members sitting at the Shabbat table. However, he records that the practice in Germany was for woman to sing Zemirot in the company of unrelated men. Rav Weinberg records that Rav Azriel Hildesheimer and Rav Samson Raphael Hirsch (two great German Rabbis of the nineteenth century) sanctioned this practice. Rav Weinberg reports that they based their ruling on the Talmudic rule (Megila 21b) that “Trei Kali Lo Mishtamai,” two voices cannot be heard simultaneously.

Rav Weinberg writes that he does not find this explanation satisfying (perhaps because the Gemara (Sotah 48a) writes that men and women singing together is a major impropriety). Rav Weinberg instead defends the German Jewish practice by citing the Sdei Chemed (Klalim, Maarechet Hakuf, 42) who quotes the Divrei Cheifetz who asserts that the Kol Isha prohibition does not apply to women singing Zemirot, singing songs to children, and lamentations for the dead. This authority explains that in these contexts men do not derive pleasure from the woman’s voice. [...]

Accordingly, the question of whether the Kol Isha prohibition applies to Zemirot remains unresolved. Chareidi communities in Israel and North America generally follow the stringent view on this matter and Modern Orthodox communities in Israel and North America generally follow the tradition of German Jewry in this regard.

It seems appropriate, though, not to expand this leniency and permit situations beyond that which the German Poskim specifically authorized – a group of men and women singing Zemirot together. Interestingly, I asked Rav Yosef Dov Soloveitchik in July 1985 whether he agrees with this ruling of Rav Weinberg.

See also this important article from R Moshe Lichtenstein on the application of these halachot to modern times (with source sheet here).

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