She/He/They/Zie/Hir: WTF Gender?
Confusion From The Very Beginning

וַיִּבְרָ֨א אֱלֹקִ֤ים ׀ אֶת־הָֽאָדָם֙ בְּצַלְמ֔וֹ בְּצֶ֥לֶם אֱלֹקִ֖ים בָּרָ֣א אֹת֑וֹ זָכָ֥ר וּנְקֵבָ֖ה בָּרָ֥א אֹתָֽם׃

And God created man in His image, in the image of God He created him; male and female He created them.

[...] אָמַר רַבִּי יִרְמְיָה בֶּן אֶלְעָזָר בְּשָׁעָה שֶׁבָּרָא הַקָּדוֹשׁ בָּרוּךְ הוּא אֶת אָדָם הָרִאשׁוֹן, אַנְדְּרוֹגִינוֹס בְּרָאוֹ, הֲדָא הוּא דִכְתִיב (בראשית ה, ב): זָכָר וּנְקֵבָה בְּרָאָם.

... Said R’ Yirmiyah ben Elazar: In the hour when the Holy One created the first human, He created him [as] an androgyne/androginos, as it is said, “male and female He created them”.

(א) אנדוגינוס יש בו דרכים שוה לאנשים ויש בו דרכים שוה לנשים ויש בו דרכים שוה לאנשים ונשים ויש בו דרכים אינו שוה לא לאנשים ולא לנשים:

(ה) רבי מאיר אומר אנדרוגינוס בריה בפני עצמה הוא ולא יכלו חכמים להכריע עליו אם הוא איש או אשה אבל טומטום אינו כן פעמים שהוא איש פעמים שהוא אשה:

(1) An Androginus (a hermaphrodite, who has both male and female reproductive organs) is similar to men in some, and to women in other ways, in some ways to both, and in some ways to neither.

Rabbi Meir Says: Androginus is a (gender/sex) category of its own, (because) the rabbis could not decipher whatever zie is a man or or a woman. However a Tumtum is not so, as at times zie is fully male, and at times zie is fully female (but we can't tell which).

(Literal translation by Abby Stein)

Fine, but at least there's clear gender Rules/Roles...
לֹא־יִהְיֶ֤ה כְלִי־גֶ֙בֶר֙ עַל־אִשָּׁ֔ה וְלֹא־יִלְבַּ֥שׁ גֶּ֖בֶר שִׂמְלַ֣ת אִשָּׁ֑ה כִּ֧י תוֹעֲבַ֛ת ה' אֱלֹקֶ֖יךָ כָּל־עֹ֥שֵׂה אֵֽלֶּה׃ (פ)

A woman must not put on man’s apparel, nor shall a man wear woman’s clothing; for whoever does these things is abhorrent to the LORD your God.

לא יהיה כלי גבר על אשה. שֶׁתְּהֵא דּוֹמָה לְאִישׁ, כְּדֵי שֶׁתֵּלֵךְ בֵּין הָאֲנָשִׁים, שֶׁאֵין זוֹ אֶלָּא לְשֵׁם נִאוּף (עי' ספרי):

ולא ילבש גבר שמלת אשה. לֵילֵךְ לֵישֵׁב בֵּין הַנָּשִׁים.

THE APPAREL OF A MAN SHALL NOT BE ON A WOMAN — so that she look like a man, in order to consort with men, for this can only be for the purpose of adultery (unchastity) (cf. Sifrei Devarim 226:1)

NEITHER SHALL A MAN PUT ON A WOMAN’S GARMENT in order to go and stay unnoticed amongst women.

הגה: מה שנהגו ללבוש פרצופים בפורים וגבר לובש שמלת אשה ואשה כלי גבר אין איסור בדבר מאחר שאין מכוונין אלא לשמחה בעלמא

Rama: [...] As to the custom of wearing 'faces' on Purim, and men who wear women's dresses and women wearing men's attire - this is not forbidden, for they have no intention other than pure pleasure.

Fine, fine, but at least the labels never change...

אשה אצל בעלה לא בעיא הסיבה ואם אשה חשובה היא צריכה הסיבה

A woman who is with her husband is not required to recline, but if she is an important woman, she is required to recline.

The Mordechai cites, in the name of the Tosafot, a novel position with important practical ramifications in this context: “If she is an important woman, she must recline. The Tosafot explain that all of our women are important and they are required to recline” (Addendum to Arvei Pesachim)

Okay okay, but we can at least agree on what to call each other, RIGHT???

In my gender class[...]a student revealed in an [journal assignment] entry that they thought they might be transgender. The next time I spoke with the student alone, with the best of intentions, I asked what pronoun they wanted me to use. Their eyes filled with tears as they answered, “I don’t know.” At about the same time, I asked someone at a conference what pronoun to use, and she burst into tears. She later explained that she had hoped that she “passed” and that my question made her feel like she did not.

-The Problem With Pronouns, Rachel Levin

https://www.insidehighered.com/views/2018/09/19/why-asking-students-their-preferred-pronoun-not-good-idea-opinion