איכה versus אַיֶּֽכָּה : How can questioning lead to understanding? An analysis of Parshat Devarim
וַיִּקְרָ֛א ה' אֱלֹקִ֖ים אֶל־הָֽאָדָ֑ם וַיֹּ֥אמֶר ל֖וֹ אַיֶּֽכָּה׃
The LORD God called out to the man and said to him, “Where are you?”
ואמר רב יהודה אמר רב אדם הראשון מין היה שנאמר (בראשית ג, ט) ויקרא ה' אלקים אל האדם ויאמר לו איכה אן נטה לבך רבי יצחק אמר מושך בערלתו היה כתיב הכא (הושע ו, ז) והמה כאדם עברו ברית וכתיב התם (בראשית ט, ט) את בריתי הפר

And Rav Yehuda says that Rav says: Adam the first man was a heretic, as it is stated: “And the Lord called to the man and said to him: Where are you”? (Genesis 3:9), meaning, to where has your heart turned, indicating that Adam turned from the path of truth. Rabbi Yitzḥak says: He was one who drew his foreskin forward, so as to remove any indication that he was circumcised. It is written here: “And they like men [adam] have transgressed the covenant” (Hosea 6:7), and it is written there: “And the uncircumcised male who is not circumcised in the flesh of his foreskin, that soul shall be cut off from his people; he has broken My covenant” (Genesis 17:14).

רַבִּי אַבָּהוּ פָּתַח (הושע ו, ז): וְהֵמָה כְּאָדָם עָבְרוּ בְרִית, זֶה אָדָם הָרִאשׁוֹן, אָמַר הַקָּדוֹשׁ בָּרוּךְ הוּא אָדָם הָרִאשׁוֹן הִכְנַסְתִּי אוֹתוֹ לְגַן עֵדֶן וְצִוִּיתִיו וְעָבַר עַל צִוּוּיִי, וְדַנְתִּי אוֹתוֹ בְּגֵרוּשִׁין וּבְשִׁלּוּחִין, וְקוֹנַנְתִּי עָלָיו אֵיכָה. הִכְנַסְתִּי אוֹתוֹ לְגַן עֵדֶן, שֶׁנֶּאֱמַר (בראשית ב, טו): וַיִּקַּח ה' אֱלֹקִים אֶת הָאָדָם וַיַּנִּחֵהוּ בְגַן עֵדֶן, וְצִוִּיתִיו, שֶׁנֶּאֱמַר (בראשית ב, טז): וַיְצַו ה' אֱלֹקִים עַל הָאָדָם לֵאמֹר וגו'. וְעָבַר עַל צִוּוּיִי, שֶׁנֶּאֱמַר (בראשית ג, יא): הֲמִן הָעֵץ אֲשֶׁר צִוִּיתִיךָ וגו', וְדַנְתִּי אוֹתוֹ בְּגֵרוּשִׁין, שֶׁנֶּאֱמַר (בראשית ג, כד): וַיְגָרֶשׁ אֶת הָאָדָם, וְדַנְתִּי אוֹתוֹ בְּשִׁלּוּחִין, שֶׁנֶּאֱמַר (בראשית ג, כג): וַיְשַׁלְּחֵהוּ ה' מִגַּן עֵדֶן, וְקוֹנַנְתִּי עָלָיו אֵיכָה, שֶׁנֶּאֱמַר (בראשית ג, ט): וַיֹּאמֶר לוֹ אַיֶכָּה, אֵיכָה כְּתִיב. אַף בָּנָיו הִכְנַסְתִּי אוֹתָם לְאֶרֶץ יִשְׂרָאֵל, שֶׁנֶּאֱמַר (ירמיה ב, ז): וָאָבִיא אֶתְכֶם אֶל אֶרֶץ הַכַּרְמֶל, וְצִוִּיתִים, שֶׁנֶּאֱמַר (ויקרא כד, ב): צַו אֶת בְּנֵי יִשְׂרָאֵל, וְעָבְרוּ עַל צִוּוּיִי, שֶׁנֶּאֱמַר (דניאל ט, יא): וְכָל יִשְׂרָאֵל עָבְרוּ אֶת תּוֹרָתְךָ, וְדַנְתִּי אוֹתָם בְּגֵירוּשִׁין, שֶׁנֶּאֱמַר (הושע ט, טו): מִבֵּיתִי אֲגָרְשֵׁם, וְדַנְתִּי אוֹתָם בְּשִׁלּוּחִין, שֶׁנֶּאֱמַר (ירמיה טו, א): שַׁלַּח מֵעַל פָּנַי וְיֵצֵאוּ, וְקוֹנַנְתִּי עֲלֵיהֶם אֵיכָה יָשְׁבָה בָדָד.
...Rabbi Abahu opens “And they, to a person, transgressed the covenant” (Hosea 6:7). This is the first person, said the Kadosh Baruch Hu, the first person that I put into Gan Eden, and I commanded them and they transgressed my commands and I judged them according to exile and banishment, and I mourned for them, [saying] “How!?”I put them in Gan Eden, as it says “Hashem Elohim took the person and left them in Gan Eden” (Breishit 2:15), and commanded them, as it says “Hashem God commanded the person, saying….” (Breishit 2:16). And the person transgressed my commandments, as it says “And what about the tree that I commanded you about [did you eat from it?]...” (Breishit 3:11), and I judged them according to exile, as it says “[God] drove the person out…” (Breishit 3:24), and I judged the person according to banishment, as it says “Hashem banished them from Gan Eden” (Breishit 3:23), and I mourned them, crying “where”, as it says “[God] said to them ‘Where.’” (Breishit 3:9). “איכה” is written. Therefore only his son entered with him to the land of Israel, as it says “I brought you to the farmland” (Jeremiah 2:7) and commanded them, as it says “Command the Israelites” (Vayikra 24:2) and they transgressed my commandments, as it says “All of the Israelites have transgressed Your Torah” (Daniel 9:11), and I judged them according to exile, as it says “From my house, I will divorce them” (Hosea 9:15), and I judged them according to banishment, as it says “Banish them from my presence and let them go out” (Jeremiah 15:1), and I mourned them “How it dwells alone” (Lamentations 1:1).
איכה, אמר כן לפתיחת הדברים כמו אי הבל אחיך (ד' ט') מזה בידך (שמות ד' ב'):
ויקרא..איכה, He called out “where are you?” G’d used these words as an opener for the conversation, not because He was unaware of their whereabouts. We find a repeat of this when G’d opened His conversation with Kayin (Genesis 4,9) or with Moses (Exodus 4,2).
איכה. יוֹדֵעַ הָיָה הֵיכָן הוּא אֶלָּא לִכָּנֵס עִמּוֹ בִּדְבָרִים, שֶׁלֹּא יְהֵא נִבְהָל לְהָשִׁיב אִם יַעֲנִישֵׁהוּ פִּתְאוֹם (בראשית רבה), וְכֵן בְּקַיִן אָמַר לוֹ אֵי הֶבֶל אָחִיךָ (בראשית ד), וְכֵן בְּבִלְעָם מִי הָאֲנָשִׁים הָאֵלֶּה עִמָּךְ (במדבר כ"ב), לִכָּנֵס עִמָּהֶם בִּדְבָרִים, וְכֵן בְּחִזְקִיָּה בִּשְׁלוּחֵי מְרֹאדַךְ בַּלְאֲדָן:
איכה WHERE ART THOU — He knew where he was, but He asked this in order to open up a conversation with him that he should not become confused in his reply, if He were to pronounce punishment against him all of a sudden. Similarly in the case of Cain, He said to him, (4:9) “where is Abel thy brother?” Similarly with Balaam, (Numbers 22:9) “what men are these with thee?” — to open up a conversation with them; so, also, in the case of Hezekiah with reference to the messengers of Merodach-baladan (Isaiah 39:3).
אֵיכָ֥ה אֶשָּׂ֖א לְבַדִּ֑י טָרְחֲכֶ֥ם וּמַֽשַּׂאֲכֶ֖ם וְרִֽיבְכֶֽם׃
How can I bear unaided the trouble of you, and the burden, and the bickering!

רבי אבהו פתח, והמה כאדם עברו ברית (הושע ו, ז), זה אדם הראשון. אמר הקב"ה, אדם הכנסתי אותו לגן עדן וציויתיו, ועבר על ציווי ודנתי אותו בגירושין ובשלוחין וקוננתי עליו איכה כו'. עד הכנסתי אותם לארץ ישראל, שנאמר (ירמיה ב, ז) ואביא אתכם אל ארץ הכרמל. וציויתים, שנאמר (ויקרא כד, ב) צו את בני ישראל. ועברו על ציווי, שנאמר (דניאל ט, יא) וכל ישראל עברו תורתיך. ודנתם בגירושין, שנאמר (הושע ט, טו) ומביתי אגרשם. בשלוחין שלחם מעל פני כו' איכה:

Rabbi Abahu saying that G–d describes how he had placed Adam into Gan Eden, commanded him a single commandment, which he transgressed. G–d consequently punished him with expulsion and personally elegized him with the word איכ-ה, Ayekkoh, (Genesis 3,9), which can be read as Eychah, an expression of mourning as in Lamentations, and also as used by Moses in Deut. 1,12 in the same sense, until He was able to bring the Jewish people into the Holy Land. Jeremiah 2,7 describes this in the words ואביא אתכם אל ארץ הכרמל לאכול את פריה. "I have brought you to the land of the Carmel to eat its fruit." Proof that G–d commanded Israel to observe commandments in the Holy Land is derived from Numbers 34,2: "Command the children of Israel, say to them…when you enter the land of Canaan, etc." Israel transgressed these commandments as described in Daniel 9, 9-11. Daniel includes the whole people as having violated G–d's teachings, as a result of which the curses in the Torah were poured out over them. Our exile, too, was a result of such conduct as is stated in Hoseah 9,9: "I will expel them from My House." The expulsion was not only to a country adjoining their homeland, but also to far off places as is indicated by Jeremiah 15,1: שלח מעל פני ויצאו, "Dismiss them from My Presence; let them go forth!" In His elegy, G–d refers to the lonely and isolated situation Zion finds itself in as a result; cf. Lamentations 1,1. Thus the introduction of Midrash Eicha.

במדרש (איכה רבתי פ"א) אמר רבי לוי שלשה אמרו בלשון איכה. משה. ישעיהו. ירמיהו. משל מה הדבד דוה למטרונה שהיו לה ג' שושנינין אחד ראה אותה בשלותה ואחד ראה אותה בפחזותה. ואחד ראה אותה בניוולה , כך משה ראה אותן בשלותן אמר איכה אשא לבדי טרחכם ומשאכם וריבכם. ישעיהו ראה אותן בפחזותן אמר איכה היתה לזונה וגו' (ישעי' א') ירמיהו ראה אותה בניוולה אמר איכה ישבה בדד (איכה א'):
Midrash Eychah Rabbati 1, relates in the name of Rabbi Levi: "Three people used the term eychah, Moses, Isaiah and Jeremiah." This could be understood by the following parable. A lady of substance had three intimate friends. One of the friends knew her when she was at the height of her beauty and wealth. The second friend knew her while she was committing all manner of excesses, over indulgence etc. The third friend knew her only when she had already fallen into disgrace. Thus, Moses saw Israel at peace, and at a high level spiritually. Yet he proclaimed "How can I alone carry the burden of your quarrels etc." (Deut 1,12) Isaiah, who knew Israel at a time when she committed all kinds of excesses, proclaimed "how has she become a harlot." (Isaiah 1,21) Jeremiah who knew Israel in disgrace proclaimed: "How lonesome and isolated has she become!" (Lamentations 1,1)
איכה אשא לבדי טרחכם. הטורח שיש לי שאשכיל המצות לפתאים. ודרשו רז"ל מלמד שהיו ישראל טרחנין הרבה, אחד מהם רואה בעל דינו נוצח בדין אמר יש לי עדים להביא יש לי ראיה להביא מוספני עליכם דיינין.
איכה אשא לבדי טרחכם, “How am I able to carry alone the trouble of you, and the burdens, etc.” The “trouble” Moses was referring to was that he had to explain the meaning of the commandments to foolish people. Our sages in Sifri Devarim 12 explain that the Israelites were bothering Moses with a great deal of litigation and the loser in litigation would never be content with the judgment but would claim that he had witnesses whom he had not presented, arguments which he had not used, etc., all in order to reopen the matter. Moses would have to add more judges to review the case.
איכה אשא וגו'. היא גזירת מאמר לא אוכל, אלא שהפסיק בענין להרים מכשול הנמשך מדיבור לא אוכל לבדי וגו' כמו שפירשתי, וחזר להשלים הדיבור שהתחיל לומר ואמר איכה אשא וגו' הבו לכם וגו':
איכה אשא לבדי, "How can I bear alone, etc.?" Moses now reverts to what he had said in verse 9: "I cannot bear you myself alone." He had interrupted this train of thought in order to counteract any negative results which would accrue to the people from a complaint about them by their leader. At this point he feels it is safe to carry on with what he had to say in verse 9.
איכה אשא לבדי. אִם אֹמַר לְקַבֵּל שָׂכָר, לֹא אוּכַל, זוֹ הִיא שֶׁאָמַרְתִּי לָכֶם לֹא מֵעַצְמִי אֲנִי אוֹמֵר לָכֶם אֶלָּא מִפִּי הַקָּבָּ"ה:
איכה אשא לבדי HOW CAN I MYSELF ALONE BEAR [YOUR CUMBRANCE, etc.]? — If I were to say, "I will do so in order to receive a reward for it", I may not do so. This is what I have already said to you: not of myself do I tell you that I am not able to bear you, but by the bidding of the Holy One, blessed be He (see Rashi v. 9).
אֵיכָ֣ה ׀ יָשְׁבָ֣ה בָדָ֗ד הָעִיר֙ רַבָּ֣תִי עָ֔ם הָיְתָ֖ה כְּאַלְמָנָ֑ה רַּבָּ֣תִי בַגּוֹיִ֗ם שָׂרָ֙תִי֙ בַּמְּדִינ֔וֹת הָיְתָ֖ה לָמַֽס׃ (ס)
Alas! Lonely sits the city Once great with people! She that was great among nations Is become like a widow; The princess among states Is become a thrall.
אֵיכָה֙ הָיְתָ֣ה לְזוֹנָ֔ה קִרְיָ֖ה נֶאֱמָנָ֑ה מְלֵאֲתִ֣י מִשְׁפָּ֗ט צֶ֛דֶק יָלִ֥ין בָּ֖הּ וְעַתָּ֥ה מְרַצְּחִֽים׃
Alas, she has become a harlot, The faithful city That was filled with justice, Where righteousness dwelt— But now murderers.