Awkward: What do we do with challenging texts in the Torah?
In theory...
(יז) דְּרָכֶ֥יהָ דַרְכֵי־נֹ֑עַם וְֽכָל־נְתִ֖יבוֹתֶ֣יהָ שָׁלֽוֹם׃ (יח) עֵץ־חַיִּ֣ים הִ֭יא לַמַּחֲזִיקִ֣ים בָּ֑הּ וְֽתֹמְכֶ֥יהָ מְאֻשָּֽׁר׃ (פ)
(17) Her ways are pleasant ways, And all her paths, peaceful. (18) She is a tree of life to those who grasp her, And whoever holds on to her is happy.
... but in practice:
(א) וַיְהִ֗י אַחַר֙ הַדְּבָרִ֣ים הָאֵ֔לֶּה וְהָ֣אֱלֹקִ֔ים נִסָּ֖ה אֶת־אַבְרָהָ֑ם וַיֹּ֣אמֶר אֵלָ֔יו אַבְרָהָ֖ם וַיֹּ֥אמֶר הִנֵּֽנִי׃ (ב) וַיֹּ֡אמֶר קַח־נָ֠א אֶת־בִּנְךָ֨ אֶת־יְחִֽידְךָ֤ אֲשֶׁר־אָהַ֙בְתָּ֙ אֶת־יִצְחָ֔ק וְלֶךְ־לְךָ֔ אֶל־אֶ֖רֶץ הַמֹּרִיָּ֑ה וְהַעֲלֵ֤הוּ שָׁם֙ לְעֹלָ֔ה עַ֚ל אַחַ֣ד הֶֽהָרִ֔ים אֲשֶׁ֖ר אֹמַ֥ר אֵלֶֽיךָ׃ (ג) וַיַּשְׁכֵּ֨ם אַבְרָהָ֜ם בַּבֹּ֗קֶר וַֽיַּחֲבֹשׁ֙ אֶת־חֲמֹר֔וֹ וַיִּקַּ֞ח אֶת־שְׁנֵ֤י נְעָרָיו֙ אִתּ֔וֹ וְאֵ֖ת יִצְחָ֣ק בְּנ֑וֹ וַיְבַקַּע֙ עֲצֵ֣י עֹלָ֔ה וַיָּ֣קָם וַיֵּ֔לֶךְ אֶל־הַמָּק֖וֹם אֲשֶׁר־אָֽמַר־ל֥וֹ הָאֱלֹקִֽים׃
(1) Some time afterward, God put Abraham to the test. He said to him, “Abraham,” and he answered, “Here I am.” (2) And He said, “Take your son, your favored one, Isaac, whom you love, and go to the land of Moriah, and offer him there as a burnt offering on one of the heights that I will point out to you.” (3) So early next morning, Abraham saddled his ass and took with him two of his servants and his son Isaac. He split the wood for the burnt offering, and he set out for the place of which God had told him.
Eliezer Berkovits, Not In Heaven: the nature and function of halachah, p. 1-2
Halacha is the bridge over which the Torah moves from the written word into the living deed. Normally, there is a confrontation between the text, which is set, and life, which is forever in motion. (...) How to face the confrontation between the text and the actual life situation, how to resolve the problems arising out of this confrontation, is the task of the torah shebeal peh, the Oral Law. This second Torah, ever since the days of Moses, handed down from generation to generation, accompanies the torah shebichtav, the Written Word. (...) Since there is no such thing as life in general, since it is always a certain form of life at a specific time in history, in a specific situation, Torah application means application to a specific time in a specific situation. The result of this process is what I call halachic Judaism.
What's a Jew to do? Below are several possible approaches one could have when hitting moral roadblocks. Most of them are from the Talmud. Try and identify what the strategy is each time - and discuss with your chavruta whether you think it works for you, and whether it works for Judaism.
א"ר יוסי בר' חנינא אין דברי תורה מתקיימין אלא במי שמעמיד עצמו ערום עליהן שנאמר אני חכמה שכנתי ערמה א"ר יוחנן אין דברי תורה מתקיימין אלא במי שמשים עצמו כמי שאינו שנאמר (איוב כח, יב) והחכמה מאין תמצא
Rabbi Yosei, son of Rabbi Ḥanina, says: The matters of Torah do not endure except in one who stands naked for them, as it is stated: “I, wisdom, dwell with nakedness [orma]” (Proverbs 8:12). Rabbi Yoḥanan says: The matters of Torah do not endure except in one who considers himself as one who does not exist, as it is stated: “But wisdom, it can be found in nothingness” (Job 28:12).
(כב) בֶּן בַּג בַּג אוֹמֵר, הֲפֹךְ בָּהּ וַהֲפֹךְ בָּהּ, דְּכֹלָּא בָהּ.
(22) Ben Bag Bag said:Turn it over, and [again] turn it over, for all is therein.
אמר רבי מנא: כי לא דבר רק הוא מכם. ואם הוא רק, מכם הוא. למה? שאין אתם יגיעין בתורה.
Rabbi Mana quotes: "and the Torah is not empty for you (litterally: because of you)" (Deut 32:47). If it's empty, it's because of you. Why? Because you don't work it enough.
אמר רבי אבא אמר שמואל שלש שנים נחלקו בית שמאי ובית הלל הללו אומרים הלכה כמותנו והללו אומרים הלכה כמותנו יצאה בת קול ואמרה אלו ואלו דברי אלקים חיים הן והלכה כבית הלל
Rabbi Abba said that Shmuel said: For three years Beit Shammai and Beit Hillel disagreed. These said: The halakha is in accordance with our opinion, and these said: The halakha is in accordance with our opinion. Ultimately, a Divine Voice emerged and proclaimed: Both these and those are the words of the living God. However, the halakha is in accordance with the opinion of Beit Hillel.
היכא דאפשר אפשר היכא דלא אפשר לא אפשר
Where it is possible to examine the situation it is possible; where it is not possible, it is not possible.
אין גוזרין גזירה על הצבור אא"כ רוב צבור יכולין לעמוד בה
We do not issue a decree upon the public unless a majority of the public is able to abide by it
אמר ריש לקיש פעמים שביטולה של תורה זהו יסודה דכתיב (שמות לד, א) אשר שברת אמר לו הקב"ה למשה יישר כחך ששברת
Reish Lakish says: Sometimes the cancelation of Torah is its foundation, e.g., if one breaks off his studies in order to participate in a funeral or a wedding procession. This is derived from a verse, as it is written: “And the Lord said to Moses: Hew for yourself two tablets of stone like the first, and I will write upon the tablets the words that were on the first tablets, which [asher] you broke” (Exodus 34:1). The word “asher” is an allusion to the fact that that the Holy One, Blessed be He, said to Moses: Your strength is true [yishar koḥakha] in that you broke the tablets, as the breaking of the first tablets led to the foundation of the Torah through the giving of the second tablets.
Rabbi Ethan Tucker, "Redeeming the Akeidah, Halakhah, and Ourselves", Summary, 2015 - https://www.hadar.org/torah-resource/redeeming-akeidah-halakhah-and-ourselves
But human sacrifice was not murder to him, even if it seems so to us. And yet, we have many analogues today to the sacrifice Avraham was ready to perform, and these are not in conflict with our broader ethical commitments. Who would think that the parents who sent their children to certain death on the beaches of Normandy were ethically lapsed? When we believe a cause is just and is of ultimate significance, the willingness to die—and even to put others at risk—is rightly understood as heroic, not immoral. (...) The consequences for how we approach halakhah are clear. God would not command Avraham—and does not command us—to do things that we understand to be immoral. When we experience a gap between our understanding of the divine will and the ethical imperative, something is in need of fixing. It is possible that our ethical instincts are wrong and must be refined. Alternatively, we may have incorrectly understood the divine will or incorrectly applied it to our lives. A deep process of learning and searching may be required to narrow that gap to zero, but eliminated it must be. The process of halakhah can never end in a place where God and morality are in conflict and the job of the learner—and certainly the posek—is to understand how apparent conflicts are incomplete understandings. There is no possibility of rebellion against God’s word, because God’s human servants know that the divine word is meant to be fully compatible with who they are meant to be. Observing mitzvot is at times exceedingly hard and requires great sacrifice and investment. But the figure of Avraham, properly understood, provides no support for the notion that God’s command is ever meant to supersede our ethics.

Simone de Beauvoir, The Ethics of Ambiguity, 1947
There was Stalingrad and there was Buchenwald, and neither of the two wipes out the other. Since we do not succeed in fleeing it, let us therefore try to look the truth in the face. Let us try to assume our fundamental ambiguity. It is in the knowledge of the genuine conditions of our life that we must draw our strength to live and our reason for acting...
In order for the return to the positive to be genuine it must involve negativity, it must not conceal the antinomies between means and end, present and future; they must be lived in a permanent tension; one must retreat from neither the outrage of violence nor deny it, or, which amounts to the same thing, assume it lightly. (...) But we also think that what distinguishes the tyrant from the man of good will is that the first rests in the certainty of his aims, whereas the second keeps asking himself, “Am I really working for the liberation of men? Isn’t this end contested by the sacrifices through which I aim at it?”
(ה) וּשְׁמַרְתֶּ֤ם אֶת־חֻקֹּתַי֙ וְאֶת־מִשְׁפָּטַ֔י אֲשֶׁ֨ר יַעֲשֶׂ֥ה אֹתָ֛ם הָאָדָ֖ם וָחַ֣י בָּהֶ֑ם אֲנִ֖י ה'׃ (ס)
(5) You shall keep My laws and My rules, by the pursuit of which man shall live: I am the LORD.
(ויקרא יח, ה) וחי בהם ולא שימות בהם
When the verse specified to you: “You shall keep My statutes…which a man shall do and live by them” (Leviticus 18:5) - and not that he should die by them,
(יט) הַעִידֹ֨תִי בָכֶ֣ם הַיּוֹם֮ אֶת־הַשָּׁמַ֣יִם וְאֶת־הָאָרֶץ֒ הַחַיִּ֤ים וְהַמָּ֙וֶת֙ נָתַ֣תִּי לְפָנֶ֔יךָ הַבְּרָכָ֖ה וְהַקְּלָלָ֑ה וּבָֽחַרְתָּ֙ בַּֽחַיִּ֔ים לְמַ֥עַן תִּחְיֶ֖ה אַתָּ֥ה וְזַרְעֶֽךָ׃
(19) I call heaven and earth to witness against you this day: I have put before you life and death, blessing and curse. Choose life so that you and your offspring will live