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My sister lives in Williamsburg, Brooklyn, New York City, and the neighborhood has a large population of Orthodox Jews and, I think, Hassidim (I don't really understand the difference, but that is a subject for another question). She has two kids, both young, and when they were babies, she would sometimes sing to them as she pushed the stroller or rode the bus or subway.

She frequently noticed that when she sang, Orthodox Jewish men would give her nasty looks. She didn't care very much, because it was a public place and there aren't any laws against singing, but I am curious as to why she got the "stink eye".

I heard some vague rumors about Orthodox Judaism and women singing, but I haven't been able to find any conclusive evidence one way or the other. Poking around on this site, I came across this quote:

The Sedei Hemed was relying on the Divrei Heifetz (113b), who "stated that as long as a woman is not singing sensual love songs, and as long as a man does not intend to derive pleasure from her voice, there is no prohibition, such as if she is... singing a lullaby to a baby, or is wailing at a funeral." [4] Rabbi Weinberg also cited the Sefer ha-Eshkol (Hilkhot Tefillah sec. 4 or 7), that listening to a woman sing is prohibited only where there is sexual pleasure. Rabbi Weinberg reasoned that if the Sedei Hemed could permit funeral dirges due to their lacking sexual pleasure, then he could permit Shabbat zemirot on the same grounds. It is obvious that we today can likewise permit by the same logic any song which does not lead to sexual thoughts. Thus, this interpretation that kol ishah is like etzba ketana, i.e. permitted where sexual pleasure is absent, is not only apparent from the simple meaning of Rambam's words, but is also endorsed by Rabbi Yehiel Weinberg.
- Source, cited in this answer

My sister's singing obviously falls under the category of singing a lullaby to a baby, so it would seem that some people agree that there isn't a problem with it.

Is there a reason why Orthodox Jewish men seemed to take offense at my sister singing?

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    Not everyone agrees to that quote... – Double AA Aug 19 '15 at 15:50
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    As I recall, the S'dei Chemed said not to rely on the Divrei Cheifetz in practice, though that quote is correct that the S'ridei Eish (Rabbi Weinberg) included this as one factor to permit mixed youth groups singing Shabbat songs together. (Incidentally, I don't think "sensual love songs" is the most accurate translation for what the Divrei Cheifetz was talking about. He was seemingly referring to romantic songs in general, not only to especially sensual ones). Also, as @DoubleAA noted, not everyone accepts this leniency. – Fred Aug 19 '15 at 20:19
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    I don't want to put down other Jews, but I need to point out one thing. While I, and many other orthodox Jews wouldn't want to listen (it seems the answers addressed this, though I haven't read them); nevertheless, giving nasty stares in most orthodox Jews' opinion is worse. For reasons of derech eretz (acting with respect) and chilul Hashem (disgracing G-d; by acting in a not nice manner).... – user613 Aug 19 '15 at 23:23
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    ...Also, your sister is allowed to sing, they just shouldn't be listening. Williamsburg is known as one of the extreme neighborhoods, and most of them haven't had much interaction with non-Jews and don't know how to relate people who aren't on their "level". – user613 Aug 19 '15 at 23:24
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    @user613 That is the focus of this linked question. – Fred Aug 20 '15 at 1:05
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The Parameters of Kol Isha by Rabbi Howard Jachter addresses this. See the full article for the details, but here are some excerpts:

The Gemara (Berachot 24a) states, “The voice of a woman is Ervah, as the Pasuk [in Shir Hashirim 2:14] states ‘let me hear your voice because your voice is pleasant and appearance attractive.’” Rashi explains that the Pasuk in Shir Hashirim indicates that a woman’s voice is attractive to a man, and is thus prohibited to him. [...]

Both Rav Ovadia Yosef (ibid) and Rav Yehuda Henkin (Teshuvot Bnei Banim 3:127) reject the claim that this prohibition does not apply today since men nowadays are accustomed to hear a woman’s voice. These authorities explain that since the Gemara and Shulchan Aruch codify this prohibition, we do not enjoy the right to abolish it. The Gemara and its commentaries do not even hint at a possibility that this prohibition might not apply if men become habituated to hearing a woman’s voice. Thus, all recognized Poskim agree that the prohibition of Kol Isha applies today.

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The Wikipedia article on Tzniut ("modesty") contains this text about singing:

Female singing voice Orthodox Judaism In Orthodox Judaism, men are generally not allowed to hear women sing, a prohibition called kol isha.[16] The Talmud classifies this as ervah (literally "nakedness"). The majority view of halachic authorities[17] is that this prohibition applies at all times, and forbids a man to pray or study Torah in the presence of a woman who is singing, similar to other prohibitions classified as ervah.[18][19] A minority view[20] holds that the prohibition of praying or studying in the presence of kol isha applies only while reciting the Shema Yisrael prayer.[19][21]

There is debate between poskim whether the prohibition applies to a recorded voice, where the singer cannot be seen, where the woman is not known to the man who is listening and where he has never seen her or a picture of her.

There are also opinions,[18] following Samson Raphael Hirsch and Azriel Hildesheimer, that exclude singing in mixed groups from this prohibition, such as synagogue prayer or dinner-table Zemirot, based on the idea that the female voice is not distinctly heard as separate from the group in these cases (“Trei Kali Lo Mishtamai,” two voices cannot be heard simultaneously – Megila 21b).

Ask the Rabbi at Yeshiva.org.il writes

Question:

What is the law regarding women singing? How strictly is it followed?

Answer: Kol Be'Isha Erva therefore woman must refrain from singing in front of men who are not of their most direct family. Those who observe the mitzvot without compromise - do not compromise on this most specific mitzva. Rabbi Eliezer S. Weisz

Rabbi Weisz takes a stricter view that the author of the Wikipedia article and than the sources you quoted. I think that his view would be much preferred in a Chassidic community.

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