According to Bible Hub's Interlinear Bible, in
- Songs 1:6, "do not look at me"
- Songs 2:7 and 3:5, "that you do not wake and that you do not awaken love"
- likewise Songs 8:4, "do not wake and do not awaken love"
- Songs 5:8, "if you find my beloved"
the verb is masculine plural, even though the people being addressed are explicitly the יְרוּשָׁלִָ֑ם בְּנ֣וֹת ("daughters of Jerusalem", with "daughters" being a feminine plural noun).
Other points in Song of Songs where the accompanying people - who may or may not be the same "daughters of Jerusalem" - are treated grammatically as masculine plural are:
- "Eat, friends; drink, and get drunk on, love" (Songs 5:1), where both the noun "friends" and all the verbs are masculine plural.
- "How you would gaze upon the Shulammitess" (Songs 6:13), addressing those who had said "Return, return, O Shulammitess, return, return, that we may gaze upon you", who are presumably representatives of "her noble people" whom she had just mentioned; the verb "you would gaze" is masculine plural.
But despite the "daughters of Jerusalem" having a masculine plural verb, the "daughters of Zion" addressed in Songs 3:11 have a feminine plural verb! ("Go out and look, O daughters of Zion, upon King Solomon...", where both imperatives are feminine plural; the word "daughters" is the same word בְּנ֥וֹת as in "daughters of Jerusalem".) Incidentally, the previous sentence ends by mentioning the "daughters of Jerusalem".
Why are the "daughters of Jerusalem" treated as grammatically masculine? Are they all women, or not?
Would it be normal in ancient Hebrew for a crowd of women to be treated as grammatically masculine?
(And why is the situation different for the "daughters of Zion", who are treated as grammatically feminine?)
[I don't know whether the answer to this question might have some overlap with the answer to my question What are the banner-bearers in Songs 6:4 and 6:10, and why is the word feminine?, as that is also about a potentially surprising grammatical gender for a group of people (although in the other direction, namely an army being feminine plural).]