How to Actually Apologize for Yom Kippur, According to Jewish Therapists

Part of: Alma’s Guide to the High Holidays

My ninth grade boyfriend broke up with me five minutes before Hebrew class. In the span of 10 seconds — or however long it took him to utter those six words — I went from a giggling, pimply teen to a remorseful, self-hating (still pimply) 14-year-old. 

“I know you like someone else,” Julian said. 


“I’m breaking up with you.”

I was caught. I did like someone else, and he had the receipts to prove it, literally. I was flirt texting my old flame who happened to be Julian’s best friend, and the jig was up. Guilt immediately engulfed me and a wave of shame smacked me in the face. My cheek stung for months as a reminder that I can’t have my cake and eat it, too.

An ice pack didn’t cool the pain — I had to put in serious work. Months later when the High Holidays rolled around, I took the opportunity to reflect on my wrongdoings and atone for my sin before my fate was to be inscribed in the Book of Death. After hours of crafting the perfect apology text to Julian, I hit send. An immediate weight lifted from my shoulders when he forgave me. Book of Life, here I come!

That was the first and last time I took Yom Kippur seriously. But this Jewish year — 5780 — I think I have a lot to atone for. I broke up with two close friends, I broke a lover’s heart, and I sort of went on a date with the brother of a guy I was casually dating… but that’s a story for another time (turns out I’m the fucking schmuck). 

It’s been a decade since I mustered up the courage to use Yom Kippur as a prompt for making amends. Turns out apologizing is hard! And frankly, it sucks. I’m all about transparency and communication, but owning up to something terrible you did is emotionally draining. On the flip side, it also releases you from self-torment. And the cherry on top? You get inscribed in that sweet, sweet Book of Life. 

But how do you know when you should apologize? And how do you gain someone’s forgiveness? Can you do it over text? With these questions flooding my mind, I called in some back-up for help: two Jewish therapists. Sit down, grab a writing utensil, and take notes on how you, too, can properly atone for your sins. 

What caused your behavior? 

First things first, you need to sit your tuchus down and reflect. So you hurt someone and feel guilty — why? What did you do? What led you to royally fucking up? 

Dr. Matthew Mandelbaum, a psychologist in New York, says that if you can determine why you did what you did and how you feel about it, the next step becomes much easier. 

“You can figure out why you might have behaved that way and then know what to do, as opposed to being a harsh critic of yourself,” Mandelbaum tells me. “Some people criticize themselves so harshly they forget the purpose of trying to be a better person.” Important!

Set your intention.

The goal of apologizing to those you wronged during the High Holidays isn’t just to be written in the Book of Life. Well, I mean, it is, but it’s the intention that matters. If you’re apologizing just so God will erase your name from the Book of Death (or uses white out, I don’t know what writing utensil God uses), your apology means zilch. The amends you make with people should be personal and sincere — don’t just send a mass apology email to everyone in your inbox. 

A self-serving apology might not necessarily be a bad thing, though, psychologist Dr. Yana Elbert tells me. “Guilt can be a very heavy emotion to carry,” she says. 

“Forgiveness can be a very complex thing, so probably talking to a therapist could be a good idea to clarify what their intentions are, because the intention behind it is really important.” 

Even if your apology has the best of intentions, if you believe revisiting a transgression will hurt the other person even more, it’s best to leave it alone. Plot twist: You don’t have to apologize to make amends! Instead, you can take what you learned from the situation and apply it to the future. In my case, for instance, the valuable lesson I learned is that instead of trying to hook up with my boyfriend’s best friend, I should be more transparent and honest about my feelings. 

Is it the right time? 

So you decided to apologize to someone — that’s great! I’m proud of you. Before you rehearse your speech, take a step back and consider if it’s the right time to reach out to the person you hurt. Did they recently experience a loss? Are they going through some shit? If the answer is yes, even if it’s High Holiday time and you want to make things right, it might not be the best time to resurface those negative feelings. 

“You want to consider whether the apology is something beneficial,” Elbert says. “Use your judgement, think about what the other person is going through.” 

Understand they might not forgive you. 

Just because you’re trying to atone for your sins doesn’t mean the person you apologize to has to forgive you. Remember that. 

“At the end of the day, we can’t control when someone does forgive us because part of it is knowing that we come from our own best intentions, but it’s really on the other person, and sometimes people hold onto resentment,” Elbert says. 

To text or not to text? 

Texting is obviously the easiest way to confront someone. It’s also the absolute worst. Hiding behind a screen is a total cop out, in my opinion, and kind of defeats the purpose of the apology. 

Both therapists I spoke to agree that texting is the worst way to apologize to someone, but it does depend on the situation. “It might depend on the magnitude of what you’re asking forgiveness for,” Elbert says. 

If you’re apologizing for something minor, a text message would probably suffice. But something that requires a lot of emotional discussion at the very least warrants a phone call or a video chat. Facial expressions, emotions and tone get lost in translation, and you might dig yourself into a deeper hole via text message. 

Validate the person who you hurt. 

You’re almost ready to apologize — mazel tov! There’s just one last thing we need to go over: validation. 

“When we feel invalidated, it’s really hard to move on,” Elbert says. “The best way to apologize is to really validate the person and ask them questions about how they feel about what happened.” 

Mandelbaum uses the example of breaking up with someone on the street. Let’s say you feel guilty about ending your relationship in a screaming match in public, but ultimately you needed to get out of the partnership for your well being. You can apologize to your ex for publicly humiliating them while simultaneously standing your ground for what you believe in. 

“I didn’t know another effective way to do it, but the function of what I was doing was to get away,” Mandelbaum says as an example apology. “I’m sorry that I hurt you in that manner, it would have been more helpful if I did it in private.” 

In my case with Julian, I wanted our relationship to end. I no longer had feelings for him, but instead of breaking up with him I was unfaithful and shady. So I apologized for hurting him while “standing on my own two feet” — as Mandelbaum puts it. 

I wish you the best of luck in the following Ten Days of Repentance — may you be inscribed in the Book of Life!