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In מה נשתנה, first it says הלילה הזה which is זכר and then it says הלילות which is נקבה. Do any commentators theorize why it switches gender?

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    לילה is a "transgender" noun that is male, but the plural form is female. Just remember לילה טוב! morfix.co.il/לילה – Kazi bácsi Mar 13 '18 at 14:04
  • @Kazibácsi Is that correct? The singular form has a female ending, so maybe it is female, already. Maybe, it's one of those female nouns that gets a male descriptor / adjective? – DanF Mar 13 '18 at 14:11
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    @DanF Morfix considers it masculine, and I suppose (I'm not an expert) that it is decided based on the singular adjective it gets. It's not that trivial, look at the male furnitures that get feminine suffices in plural (ארון, שולחן, כסא). – Kazi bácsi Mar 13 '18 at 14:20
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    @Kazibácsi Consider also the word אב, which is most certainly masculine but takes on a feminine plural: אבות. – ezra Mar 13 '18 at 15:01
  • I only see the word לילה used with masculine adjectives: לילה (ה)הוא (Bereishis 19:33,35, 26:24, 30:16, 32:14,23, Shemos 12:30, Bamidbar 14:1), לילה אחד (Bereishis 40:5, 41:11), לילה הזה (Shemos 12:8,12,42), etc. Even as the plural: שלשה לילות (Shmuel 1:30:12, Yonah 2:1). – DonielF Apr 15 at 1:29
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R. Eliyahu of Vilna (the Vilna Gaon) is quoted as having asked this question. A presentation of his approach (excerpted below) by R. Mordecai Kornfeld, can be found here:

In fact, notes the Gaon, the night is feminine in its very essence. It is for this reason, the Gaon explains, that many positive commandments ("Thou shalt...," as opposed to negative commandments -- "Thou shalt not...") must be performed exclusively during the daytime. (Examples of these are blowing the shofar on Rosh Hashanah, holding the four species on Sukkot, wearing Tzitzit and Tefillin, etc.) This is in accordance with the "feminine" nature of the night. Just as women are exempt from fulfilling these positive commandments (see Mishnah Kiddushin, 29a), so too, the night, in its role as "female," is "exempted" from all those Mitzvot. The exceptions to this general rule are the Mitzvot performed on the seder night: the eating of Matzah, Maror [= bitter herbs] and (in former -- and future -- times) the paschal lamb; and relating the story of the Exodus. The Torah earmarks these commandments to be performed exclusively at night. (It may be noted that the Mitzvot of the night of Pesach apply to women as well, even though positive commandments that are holiday-related generally do not apply to women -MK.)

This, asserts the Gaon, is the deeper meaning of the Haggadah's question: Why is this night (HaLaylah) "masculine" (HaZeh) in its properties, being laden with positive Mitzvot, whereas all other nights are feminine in nature?

[As an aside, and as noted by Kazi bácsi in a comment to the OP, the question of the Vilna Gaon is very difficult to understand in the first place. לילה, despite its plural form of לילות, is clearly a masculine noun, and always appears in Tanakh with masculine adjectives. R. Kornfeld in the linked article presents a possible approach to understand the intent of the Vilna Gaon.]

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    Besides this great answer, please note that it is feminine in German (die Nacht, די נאַכט), Romance (la notte, la nuite) and Slavic languages (ночь, ноћ). This must have puzzled the Gra. – Kazi bácsi Mar 13 '18 at 14:32
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There are words in Tanakh that are sometimes masculine and sometimes feminine, but לילה is not one of them. לילה is masculine and לילות is masculine. The form usually indicates the gender but is not definitive. Kazi's is good advice: the adjective will indicate the noun's gender. There is no such thing as a feminine noun that takes a masculine adjective. With all respect to the Gaon, I don't think he was offering a grammatical explanation.

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The general rule for feminine nouns ending in ה is that they have a kamatz gadol followed by a ה. Also, the stress is on the final kamatz-ה sequence (i.e. the ultimate syllable). The stress on לילה is on the penultimate (second-to-last) syllable (i.e. the first ל). The final kamatz-ה is probably the locative ה which expresses movement towards or into (so לילה would technically be rendered as “into the night”) as a substitute for אל or ל (as Rashi notes in many places). For example, we say ביתה, מצרימה, ירושלימה, הרה, etc.. The word for night is actually ליל (patach under 1st ל and chirik under the י). I can’t find the nekudot on my phone so I have to spell it out. We find the phrase ליל שימורים with ליל in construct form and thus having tseirei beneath the first ל as is the normal vowel change from absolute to construct for all nouns with dual endings.

  • Locative ה is always a מפיק ה, as in the cases you cite. לילה has a ה רפה. – DonielF Apr 15 at 1:19
  • The word isn't לַיִל. No such word appears in Tanach. The word is לילה, and as a construct it becomes לֵיל. – DonielF Apr 15 at 1:32
  • @Doniel מצרימה does not end with מפיק ה – Joel K Apr 15 at 3:29
  • @DonielF Regarding ליל see Yeshiyahu 16:3, the כתיב for Eichah 2:19. See Strong’s lexicon entry 3915. If you actually look at any occurrence in tanach of the locative you will not find mappik hey. – הבלשן Apr 15 at 4:31

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