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The month of Elul ushers in a period of intensive introspection and urgent repentance that culminates with the yamim noraim (days of awe), Rosh Hashanah and Yom Kippur. The fact that we sound the shofar until Rosh Hashanah and cap our prayers with the psalm 27, Le-David Hashem Ori ve-Yishi, during this period highlights the broader effort to stimulate a meaningful awakening (see Rambam, Hilchos Teshuvah 3:4 -"uru yesheinim mi-shinatchem") to repentance.
We have noted elsewhere (The Significance of Rosh Chodesh and the Month of Elul) the view cited by the Meiri (Chibbur ha-Teshuvah, p. 250) that "Dirshu Hashem behimazeo kerauhu bihiyoto karov", alluding to Hashem's increased accessibility, refers not only to the period between Rosh Hashanah and Yom Kippur (Rosh Hashanah 18b) but to the entire month of Elul. We have suggested that the relationship between Elul and the yamim noraim is a dialectical one. While Elul necessarily focuses on preparation for the yamim noraim, the proximity of yom ha-zikaron and yom ha-din and the history of Elul during the aftermath of the egel ha-zahav transgression, provide an incentive and climate particularly conducive to developing certain facets of avodat Hashem that are also integral to teshuvah.
The special emphasis of Elul is perhaps reflected in the primary motif of the ubiquitous Le-David Hashem Ori. The Malbim (27:1,4,7,12) notes that this psalm exclusively accentuates the desire for an enduring and deeper connection to Hashem. It conveys the theme that devekut ba-Hashem (clinging to the Divine) is the ultimate goal rather than a means to some other end. Achieving a genuine relationship with Hashem eclipses all other interests; all other requests are significant only to the extent that they facilitate the enhancement of this relationship. "Achat sha-alti mei-eit Hashem oto avakesh shivti be-veit Hashem kol yemei chayaiy…" encapsulates the simple but profound ambition to attain that relationship. Perhaps this theme is underscored repeatedly during Elul because Elul is the time in which the relationship between Hashem and Kelal Yisrael was reinstated and also refashioned in the aftermath of the sin of the egel, as Moshe ascended the heavens to receive the reworked second luchot. The Tur (581) explains that "alah Hashem be-teruah" (Psalm47) refers to Hashem's elevation in response to Kelal Yisrael's formal renunciation of the idolatry that doomed the first luchot and jeopardized the entire relationship.
Against this background, we can better appreciate the Abudraham's thesis that Elul is an acronym that conveys the reciprocal love of Hashem and the Jewish people ("ani le-dodi ve-dodi li") that is at the core of this relationship. The entire thrust of Shir ha-Shirim is based upon the premise of mutual love and affection between Hashem and his nation. Chazal consistently develop this theme. Mattan Torah is perceived as a kind of marriage contract. The twenty four books that comprise the canon of Torah she-biktav are compared to the jewels that adorn a bride (ke-kalah ha-mekushetet). Moreover, this intense bond transcends marriage, as it is irrevocable (See Rav Soloveitchik, Family Redeemed, p.63). The verse in Hoshea (2:21) attests to the permanence of the marriage -"ve-eirastich le-olam". In Eichah (1:1), the abandonment of Yerushalayim and the rejection of the nation is compared to a widow, not a divorcee, and even that comparison is imprecise ("ke-almanah"- see Rashi). The prophet Isaiah (50:1) remonstrates with the nation, reminding them that Hashem never divorced/rejected the nation; it was their improper behavior that alienated them from Him.
Elul focuses particularly on reasserting and refining the relationship between Hashem and Kelal Yisrael founded upon intense ahavat Hashem and rooted in reciprocity. The perspective of irrevocable mutual love and reciprocal commitment implied by "ani le-dodi ve-dodi li", reinforced by the "achat shaalti mee-eit Hashem" of Le-David Hashem ori, and the reformulated contract of the second luchot evoked by the daily shofar also contributes significantly to the effectiveness of repentance in preparation for the yamim noraim. Authentic repentance requires sincere regret (charatah), heartfelt embarrassment, and a future commitment (Rambam, Hilchot Teshuvah 1:1, 2:2). The capacity to achieve these three requirements is immeasurably enhanced by the framework of the irrevocable relationship that is reinforced during Elul. One can only truly muster deep regret and embarrassment when the relationship that is damaged is one that is indispensable to one's very existence and when the alienated party is an integral part of both one's past and future.
The gemara in Yoma (86a) distinguishes between teshuvah me-ahavah (repentance flowing from love) and teshuvah me-yirah (repentance motivated by fear). While the Rambam does not formally and explicitly register this distinction, he does reflect the centrality of ahavat Hashem in repentance in a more subtle but perhaps more profound way. The culminating chapter of Hilhot Teshuvah (ch. 10) is devoted to ahavat Hashem as a goal distinct from any functional benefit. The Rambam focuses on the method of achieving this telos and how this affects the performance of mitzvot and the study of Torah. Clearly, he intends to convey that achieving this level in the relationship with Hashem is the ultimate purpose of repentance, though it also transcends repentance. Indeed, the final chapter of repentance transitions into the Rambam's next volume, entitled Sefer Ahavah (Book of Divine Love) that is dedicated to expressing ahavat Hashem through the performance of mitzvot. It is noteworthy, that Rambam (10:3) compares the intensity and single-minded focus of ahavat Hashem to that of an all-consuming marital relationship, invoking Shir ha-Shirim. The ani le-dodi ve-dodi li theme of Elul emerges clearly.
Rav Chayim of Volozhin postulates in Nefesh ha-Chayim that teshuvah mei-ahavah is most effectively attained by increased Torah study. This idea confirms our analysis, as Torah study is the primary mechanism to engage and enhance the relationship with Hashem. The haftorah of Shabbat Shuvah emphasizes this as well- "kechu imachem devarim ve-shuvu el Hashem" (see the midrash link to kaarof kamator likchi etc.). Our obligations and opportunities in the month of Elul should inspire us to ever greater spiritual aspirations that will jointly advance our ahavat Hashem and facilitate a teshuvah sheleimah (complete repentance).