He says good-bye, and as he looks out over all the people for whom he risked his life and gave up his fortune, he began to weep. At first he cannot speak, but then he says, “I could have done more, I could have done more... This car,” he says, “why did I keep it? I could have sold it and saved ten more lives. This stupid diamond pin,” he said of a pin on his lapel, “Even that I could have sold and gotten enough money to save one more life.” Oscar Schindler kept weeping and kept repeating, “I could have done more, I could have done so much more.”

I rarely begin sermona with movie quotes, even historically-based depictions, because... they are movies, and this is real life. But the conclusion of Schindler’s List left such an ineffable impression. It’s the first time I can remember crying, well, weeping in a theatre, something that’s now the norm for me. But this scene, this frame, it’s enduring because it is an ending of deep, non-hyperbolic--from the depths of the soul--regret.

Regret.​ It’s not uncommon to hear phrases like:

“If I could do it all over again, I wouldn’t change a thing.”

“I’ve lived a life of no regrets. I never look back, only forward.”

They can be lovely sentiments. But, I think we all know, they shouldn’t really be taken seriously. At least I hope not.

Brene Brown puts it well: ​“No regrets” doesn’t mean living with courage, it means living without reflection.”

There’s no pride in that.

Regret.​ Kierkegaard once quipped: “I see it all perfectly; there are two possible situations - one can either do this or that. My honest opinion and my friendly advice is this: do it or do not do it - you will regret both.”

Regret.​ Unavoidable, yet so often, avoided.

Let’s start with what it is, and what it isn’t. And then we’ll move to why it could be, should be, the cornerstone of this day, and perhaps our future.

The origin of the English word regret comes from Old French and it means “to look back with distress or sorrowful longing.” Palpable disappointment in what has already been. It can actualize internally, or externally, and, as David Whyte so eloquently notes, “regret is a word rarely said, except when the speaker insists he has none.”

Regret ​is an admission of fallibility.

But here’s what it is not. It isn’t only remorse for what we’ve ​done​. In fact​, the science of regret suggests otherwise. Lasting regret--studies performed over the last 10 years have found--occurs not so much for the hurtful, or embarrassing things we have done, but more-so, for all of the missed opportunities.

A few days ago I arrived home from the office to find Amos, my youngest, running around the living room with Penina laughing hysterically as he hit a balloon around and watched it spin & float through the air. I joined, and it continued. It fell, he laughed. It hit my face, he fell on the floor cracking up. It hit

him, he squealed, quite literally, with delight. My heart was as full as I can remember it to be. 20 minutes of pure, embodied, bliss.

I had two immediate reactions: The first, it triggered a childhood memory of my own, one of my very earliest. My dad had come home from work with a white balloon, his clothing shop insignia, Jean’s America, imprinted on it, That’s the level of detail to which I remember this 42 year old memory -- and we spent a few minutes, not more, batting that balloon around on the side of our home. It was, and still is, a joyous, warm memory, and one of the last of its kind, that memory, as they then transition to darker memories of an embattled marriage.

The second, I felt a palpable sense of regret for every other time I’ve come home from work and gone straight to work, bypassing a likely life-affirming & love-affirming moment with my children or partner.

R​esearchers from Northwestern University in 2011 surveyed hundreds of respondents to explore their hypothesis. They assumed that when a “regretted decision ​is​ reversible, regret is ​more​ intense, and serves to motivate the individual toward a new corrective behavior.”

But they actually found the opposite to be true--they write: “individuals regret ​lost opportunities the most, particularly when, or because, they’ve failed to achieve a sense of closure following the past event.”

“Twenty years from now you will be more disappointed by the things that you didn’t do than by the ones you did do.” Mark Twain wrote. Yes, exactly.

Regret is also an essential component of this very day’s dominant theme, Teshuvah, repentance. Here’s a quick refresher course on each step:

Repentance, teshuvah, means to turn. Back to our truest selves, to God, or to whatever or from wherever we've strayed. ​This is the time of the year when we remember, especially, that we are far from perfect--that our actions, or inactions— deliberate or unintentional—have caused others, or ourselves, pain and heartache. And, this is the time of year that affirms: it doesn't have to remain this way. We just need to be willing to take the necessary steps.

Six of them​, to be precise--based on the authoritative Medieval Code of Law, Maimonides Mishneh Torah.

  1. Stop doing ​the thing you shouldn't be doing, or start doing what you should have b​een doing.
  2. Internalize regret. Obviously going to come back to this one.
  3. Confession​. To engage it, we must name it.
  4. Reconciliation ​- A sincere apology, followed by time and energy tending to the victim of our misdeed--should they be open to it.
  5. Making Amends​--what was taken must be returned. There ought to be a tangible witness to demonstrate one's sincerity, most often called: reparations.
  6. ​And, 6 ​-- the last step -- where we come full circle -- when a person confronts, again, a similar situation in which she or he sinned -- and ​has the potential​ to commit the sin again -- but nevertheless, abstains. That’s ​teshuvah gemorah, complete repentance.

Each step actually stands on its own. It’s good to just stop hurting people. Please do that. It’s worthy to confess our wrongs. Yes, make restitution.

But it’s the package, the entire process, that allows for a different, ideally better, future. Because confession without regret is somewhat empty. Reconciliation without regret is simply a bandaid. Making amends​ is ​possible, to some degree, without regret. I can still give you back what I’ve taken, but the relationship will always live with an unhealed, emotional breech.

Teshuvah is more than a series of discrete acts--it is also an emotional reckoning with what’s left lingering beneath the surface, sometimes long after the action, or inaction, has occurred.

Trevor Noah wrote in his memoir: “​regret is the thing we should fear most. Failure, is an answer. Rejection, is an answer. Regret is an eternal question you will never have the answer to.”

It’s not clean. It’s ongoing. There’s often no resolution. It requires uncertainty. Uncertainty requires courageous vulnerability. Courageous vulnerability requires at least some stability. ​And ​employed with no outlet, no healthy, affirming space to process, no loving vessel, no forgiving self to hold it, regret can easily turn into internalized shame.

You and I, we have lots of conversations about death, your lost loved ones. And sometimes you tell me about your deepest regrets--you could have done more, been there more, given more, hugged more, said more. You didn’t. And the remorse you share with me is overwhelming, because you’ve defined not only those moments of inaction through the lens of regret, but the entirety of the lost relationship--maybe even the entirety of... you. Regret can be dangerous.

Yet we must enter those straits. ​So I’m gonna bring some motivation from on high.

The very first act of regret in the Torah, and this may surprise you, comes at the beginning of Chapter 6, in Genesis. So, pretty quickly:

(ה) וַיַּ֣רְא יְהוָ֔ה כִּ֥י רַבָּ֛ה רָעַ֥ת הָאָדָ֖ם בָּאָ֑רֶץ וְכָל־יֵ֙צֶר֙ מַחְשְׁבֹ֣ת לִבּ֔וֹ רַ֥ק רַ֖ע כָּל־הַיּֽוֹם׃

(ו) וַיִּנָּ֣חֶם יְהוָ֔ה כִּֽי־עָשָׂ֥ה אֶת־הָֽאָדָ֖ם בָּאָ֑רֶץ וַיִּתְעַצֵּ֖ב אֶל־לִבּֽוֹ׃

(ז) וַיֹּ֣אמֶר יְהוָ֗ה אֶמְחֶ֨ה אֶת־הָאָדָ֤ם אֲשֶׁר־בָּרָ֙אתִי֙ מֵעַל֙ פְּנֵ֣י הָֽאֲדָמָ֔ה מֵֽאָדָם֙ עַד־בְּהֵמָ֔ה עַד־רֶ֖מֶשׂ וְעַד־ע֣וֹף הַשָּׁמָ֑יִם כִּ֥י נִחַ֖מְתִּי כִּ֥י עֲשִׂיתִֽם׃

(5) The LORD saw human wickedness flourished on earth, and how all plans devised by their minds were nothing but evil all the time.

(6) And God ​regretted​ that God had made humans on earth, and

God’s heart was saddened.

(7) The LORD said, “I will blot out from the earth the humans whom I created—humans together with beast... for I ​regret that I had made them.

Six chapters in. A few chapters after our ancestors were created, God has had... enough. Seen enough--and God’s ready to give up. Sure the Garden of Eden mistake. But one bad apple? Yes, Cain messed up. Badly. Still--It was either really just that bad, or those three chapters of humanity sleep training had really taken their toll on the All-powerful One. I can actually believe, having myself participated in three chapters of sleep training.

Let this sink in. God ​regrets​ creating humanity. God was sad--mitatzev el libo--heartbroken. I find this remarkable. It goes against almost everything we were taught in Sunday school about that all-powerful, all-knowing God. God meditates on the past, admits mistake, and is emotionally moved to regret and even experience depression.

We may not like God’s solution, utter destruction, nevertheless, it is an extraordinary moment of Divine self-reflection.

For if we truly are created in the divine image, as the Torah explicitly states when humans are created, then regret is nothing short of a divine emotion.

Part-and-parcel of who we are and ​what​ we are meant to feel--then articulate.

In biblical hebrew, you may have noticed, the root letters for regret are nun, chet, mem -- ​nachem. ​Sound familiar? It’s the same root for the word ​comfort, consolation​.

Like, ​nichum aveilim-​ -comforting mourners. ​Hamakom Yenahem Etchem, we say at the end of every funeral​. M​ay God grant you comfort.

Regret & Comfort. Which is it? Yes.

Our Sages, ​chazal, i​n an early attempt at understanding this passage (Bereshit Rabbah, 27:4), and clearly caught off-guard by it as well, also notice that the hebrew roots letters for regret and comfort are the same--but that they don’t mean the same thing in every context. Here’s how they work through it:

וַיִּנָּחֶם ה' כִּי עָשָׂה אֶת הָאָדָם בָּאָרֶץ (בראשית ו, ו), רַבִּי יְהוּדָה וְרַבִּי נְחֶמְיָה, רַבִּי יְהוּדָה אָמַר תַּוְהוּת הָיְתָה לְפָנַי שֶׁבָּרָאתִי אוֹתוֹ מִלְּמַטָּה, שֶׁאִלּוּ בָּרָאתִי אוֹתוֹ מִלְּמַעְלָה לֹא הָיָה מוֹרֵד בִּי...אָמַר רַבִּי אַיְבוּ תְּוָהוּת הָיְתָה לְפָנַי שֶׁבָּרָאתִי בּוֹ יֵצֶר הָרָע, שֶׁאִלּוּלֵי לֹא בָּרָאתִי בּוֹ יֵצֶר הָרָע לֹא הָיָה מוֹרֵד בִּי...

רַבִּי נְחֶמְיָה אָמַר מִתְנַחֵם אֲנִי שֶׁבָּרָאתִי אוֹתוֹ מִלְּמַטָּה שֶׁאִלּוּ בָּרָאתִי אוֹתוֹ מִלְּמַעְלָה כְּשֵׁם שֶׁהִמְרִיד בִּי אֶת הַתַּחְתּוֹנִים, כָּךְ הָיָה מַמְרִיד בִּי אֶת הָעֶלְיוֹנִים...

אָמַר רַבִּי לֵוִי מִתְנַחֵם אֲנִי שֶׁעָשִׂיתִי אוֹתוֹ וְנִתַּן בָּאָרֶץ.

According to Rabbi Yehuda, God thought "It was My mistake, and I regret that I created humans on earth--terrestrial beings--focusing on the superfluous word, ba-aretz-on earth. Had I created them above, in the heavenly worlds, they would not have rebelled against Me." In other words, we humans would have been more like angels, following God’s will whatever the command...

Rabbi Aivu agrees, and teaches that God "...regrets creating humans with a Yetzer ha-Ra, a wild, untamed inclination, for had God not, they would never have rebelled against God." Divine life would have been simpler without those pesky, red devils on the human shoulder.

Rabbi Nechemia disagrees -- God says: There is consolation for me. This is comforting. Because had I created them above, they would have corrupted the angels. My little obedient puppets. I’m glad I put humans below, on earth. No regrets, just comfort.

Rabbi Levi too, yes, it’s consolation, comfort. Definitely. God is "...consoled, comforted by making humans exacftly as God did, finite, mortal. They’ll eventually be, ba-aretz, literally, in the grave. And their sins will end, and God is comforted.​ Va-Yinachem.

End midrash. They don’t work it out. They can’t. Because they don’t know, our rabbis. So the answer is, yes, both. Two things can be true. God sees a personal mistake and feels either regret or comfort, or both.

Ready for this. The hebrew root has third meaning in the Torah, found in Exodus. God wants to annihilate, again, this time all the Israelites due to the Golden Calf, but Moses convinces God to pause. And God listens. Then:

וַיִּנָּ֖חֶם יְהוָ֑ה עַל־הָ֣רָעָ֔ה אֲשֶׁ֥ר דִּבֶּ֖ר לַעֲשׂ֥וֹת לְעַמּֽוֹ׃ (פ)

And God renounced, reversed, the punishment God had planned to bring upon the people.

Same root. But here it means, contextually, God changed God’s mind.

"Nehamah"​ means, also: to shift course, to see a different way:

God regrets, God is comforted. God makes mistakes. God looks to change course, and does. The path of repentance has been paved by the One who Speaks worlds into existence. For each of us, implanted with God’s Divine image, we are but lured, I believe expected, to imitate the Master of the World.

George Stephanopoulos, at a recent Town Hall noted the devastating U.S. death toll — nearly 195,000 — and simply asked P. Trump if he has any regrets about his administration's handling of the pandemic.

"No," the President replied. "I think we did a great job.”

That number is now well over 200,000, no signs of slowing down, and the President has since given himself an A+. If that kind of devastation doesn’t provoke ​any​ regret, Well, I just... I just can’t. I’m sorry.

No remorse, not an ounce of comfort, no courage, and no willingness to change course.

Brene Brown, I’ll repeat: ​“No regrets” doesn’t mean living with courage, it means living without reflection. To live without regret, she continues, is to believe you have nothing to learn, no amends to make, and no opportunity to be braver with your life.”

Juxtapose that non-regret to the integrity of Justice Ginsburg, who after making derogatory comments about then-Candidate Trump, wrote, soon after: On reflection, my recent remarks in response to press inquiries were ill-advised and I regret making them. Judges should avoid commenting on a candidate for public office. In the future I will be more circumspect."

In one article I read, legal scholars say they could not remember a time that a sitting justice expressed regret publicly for something he or she said, though many justices have had statements reported in the media.

Regret. It’s difficult. It’s also divine. And it’s definitely essential for any kind of authentic repentance--of any potential change in course, any return home, wherever it is.

That’s the beauty of one hebrew root with multiple meanings. It allows for a layered understanding of difficult concepts. Here, thanks to God, we understand that a vulnerable, honest reckoning with the past is not only courageous, not only potentially life-saving--which we need right now, but also comforting, consoling—because we can transcend ​the ​source of our remorse, or our crippling longing, our yearning for what could have been. We can change course.

It’s probably important, at this point, for me to give you a sense of what an authentic statement of regret looks like, or feels like. 13 years ago Rabbi Elianna Yolkut and I set out to build a same-sex marriage ceremony grounded in Jewish Law, Halakhah, a ceremony which has now been beautifully updated by Rabbi Holtzblatt. Our goal was to capture the legally binding essence that the traditional Jewish wedding ceremony employs, while staying true to the essence of the widely observed ceremony. The legal construct we ultimately chose was based on the biblical and rabbinic concept of.. the oath, the ​neder, ​which you all know from popular diddies like ​Kol Nidre... remember that one?

Each hattan or kallah, bride or groom--in front of their partner and witnesses-- recites an oath to abstain from all potential future intimate partners, with the exception of the one to whom they are committing their lives.

But creating a sacred way in, necessitates providing a sacred way out, if desired. A ritual to formally end the union. The method we developed for dissolution is a traditional renunciation of vows, in front of a Beit Din, a rabbinic court. And the formula relies on the very concept of regret. It’s called a ​Hatarat Nedarim,​ a releasing of vows. It goes like this:

​Listen, please, my rabbis: The vow that I vowed-- I hereby express my retroactive regret, and ask and seek its annulment from you​. ​Had I known then, what I know now, I would not have done so.

The Beit Din releases her from the vow and declares:

You are released, you are released, you are released. And just as the earthly court has granted release, so may the heavenly court grant release

This statement, said aloud, in front of witnesses, antiphonal, contains within it the foundation to regret without a fossiling, all-encompassing shame. Because it is at once: introspective, ​as well as ​self-forgiving. It doesn’t erase the past, it only seeks to reframe it with honesty, self-compassion, and an emotional path forward.

Noted clinical psychologist Dr. Darlene Mininni wrote: “​Instead of criticizing yourself for "that stupid thing I did," remember that you probably did the best you could with the information and perspective you had at the time.”

I wish I lived my own life.

I wish I’d spent more time with...

I wish I’d called more.

I wish I worked less.

I wish I was less angry.

I wish I faced that fear.

I wish I self-advocated then.

I wish I’d stepped back.

I wish I wouldn’t have left.

I wish I would have left.

I wish I wouldn’t have made it all about me when it was clearly so much bigger than me. And on & on, and so forth.

Go there. Pray on it. Cry on it. It’s really okay to cry on it. Well, more than okay, it may unlock some hidden strength. Then tell your loved one, your friend, whomever may need to hear it. Articulate your regret. Nestle it into it in its rightful place amidst your process of your ​teshuvah.

Do it with self-compassion and self-forgiveness--with some ​nechama, a consoling, comforting, courageous--regret.

And if you happen to be on the receiving end of somebody’s expression of regret, maybe pause before responding and remind yourself you are witnessing an act of bravery.

“Sincere regret,” David Whyte teaches, “may in fact be a faculty for paying attention to the future, for sensing a new tide where we missed a previous one, for experiencing timelessness with a grandchild when we neglected a boy of our own. To regret fully is to appreciate how high the stakes are in an average human life. Fully experienced, regret turns our eyes, attentive and alert to a future, possibly lived better than your past.”

Immediately after God expresses regret in Genesis 6, this happens:

(ח) וְנֹ֕חַ מָ֥צָא חֵ֖ן בְּעֵינֵ֥י יְהוָֽה׃ (פ)
(8) But Noah found favor with the LORD.

Noah was found, not ​despite​ God’s public, remorseful self-evaluation. But because​ of it. And that regret cracked God’s heart open, a necessary precondition for Noah’s righteousness to illuminate the divine capacity for recreation.

And so I ask us, what might we feel tomorrow, because of tonight’s self-openness--and what light may come through tomorrow because of tonight’s vulnerability? And what promise, what potential, what newness, might emerge the day after?

There’s really no better time than right now, Yom Kippur, for us to find out.

Gemar Hatima Tova.