Last class we kicked off a new section, taking our first look at the middle blessings of the Shemoneh Esrai and focusing on the fourth blessing of the prayer overall. That blessing, a request for intellect and wisdom, also served as the first of the personal blessings in the Shemoneh Esrai. Today, we will continue looking at the middle blessings and review the fifth blessing of the Shemoneh Esrai – the request for repentance. As always, let’s first review the actual text of the blessing:

“Bring us back, our Father, to Your Torah, and bring us near, our King, to Your service, and influence us to return in perfect repentance before You. Blessed are You, Ha-Shem, Who desires repentance.”

This blessing, a personal request that we be assisted in our repentance, logically follows the request for intellect and wisdom, as we will only come to realize that repentance is needed if we are knowledgeable. Furthermore, proper knowledge is required to ascertain where our shortcomings are before we can truly resolve to fix them.

The placement of this request also helps explain the curious introduction of this verse, where we specifically ask to be brought back to G-d’s Torah. While we should always strive to increase our learning, what does the reference to the Torah here have to do with repentance? As we noted above, only after we’ve enhanced our Torah knowledge will we have the intellectual ability to hone in on what in our lives may require repentance.

Of course, we also have to be sincere in our desire to repent. As Talelei Oros on Tefillah (citing the Dovair Shalom) points out, this is the reason we ask to be influenced to repent “Before You,” a phrase we don’t find elsewhere during Shemoneh Esrai. Only G-d is capable of knowing whether our resolve to repent is truly sincere.

The blessing also includes a request that G-d “influence us to return in perfect repentance.” Does this request not fly in the face of free will? How could we ever repent in free will if G-d is influencing us to do so?

The Migdol Dovid explains that once we have the intellectual capacity to lead us to desire repentance, we can then pray to G-d that He assist in removing those obstacles in life that may hinder our quest. The Mishna Brura agrees, noting that this request for G-d’s influence is a prayer that He help quiet our evil inclination. We are not asking G-d to interfere with our free will but, once we are willing to put in a little effort, G-d can help pave the way. As the Midrash in Shir HaShirim Rabbah says, “Make me an opening the size of a pinhole and I’ll make you an opening big enough for carriages to drive through.”

What, though, is considered a perfect repentance? Can someone repent imperfectly? One classic response is that perfect repentance is when one repents because of Ahavas Hashem, love of G-d. While one may repent due to the fear of negative consequences, perfect repentance stems only from love.

Although a number of other explanations exist, I’m partial to the one offered by Rabbi Avraham Chaim Feuer, who notes that true repentance requires one to deeply examine himself to discover the root of his negative actions. Without struggling to identify the underlying issue, one cannot truly repent.

This explanation also allows us to come full circle and offer another potential reason this blessing follows our request for knowledge and intellect. Without true knowledge, how else will we be equipped to undergo the self-examination required for perfect repentance!