Every year as the High Holidays approach, we talk about reflection, forgiveness, and teshuva (repentance). But here’s the thing: most of us are apologizing wrong. We think a quick “sorry” is enough—but Judaism says, not even close.
In this season leading up to Rosh Hashanah and Yom Kippur, Jewish tradition gives us a clear path for making things right—with God and with each other. It’s not about guilt or box-checking. It’s about repairing relationships and stepping into the new year with integrity.
In this post (and video), I’ll walk you through how to apologize like a Jew, when not to apologize, and why Yom Kippur can’t do all the heavy lifting for you.
As we enter the new year, apologies and teshuva are just one piece of the bigger picture. The High Holidays can feel overwhelming—but they don’t have to. With the right preparation, you can step into Rosh Hashanah and Yom Kippur feeling grounded, not scattered.
💙 That’s why I created The Essential Jewish Holiday Planning Guide—full of checklists, prompts, and practical tools to help you find your own “good enough” for this season. You can download it here.
Transcript below.
Transcript:
Think saying sorry is enough? Judaism says, not even close.
Here’s how to apologize like a Jew… and when you shouldn’t apologize at all.
As we head into the Jewish New Year, this season is all about reflection, forgiveness, and repairing relationships.
But Jewish tradition has a very particular way of approaching apologies, and it’s not just about saying sorry.
The Jewish New Year isn’t about resolutions, it’s about apologies.
Hi, I’m Kochava. I’m a Jewish convert who’s been helping people convert to Judaism since 2010 through my blog, Building a Jewish Life.com.
In Judaism, the High Holiday season from Rosh Hashanah through Yom Kippur is our annual deep dive into reflection and accountability.
It’s not just about prayer, it’s about repairing relationships.
In Jewish tradition, we actually split mistakes into two categories.
The first is called bein adam la-Makom. I’m sure I’m pronouncing it terribly. If you’ve been around here, you know my Hebrew’s terrible. It literally means between a person and God.
These are things like eating something treif, not kosher, skipping a prayer, or breaking a vow you made before God.
On Yom Kippur, those are the kinds of mistakes we bring directly to God through prayer, fasting, and reflection.
The second is called bein adam la-chavero, between a person and their fellow.
These are the harms we cause to other people: harsh words, broken promises, speaking Lashon Hara (harmful speech like gossip), embarrassing someone, and financial dishonesty. And here’s the key: Yom Kippur can’t wipe those away.
For those, you have to go directly to the person involved, apologize, and try to repair the relationship.
That’s why in Judaism, apologies aren’t just about good manners. It’s Halakha (Jewish law), a commandment.
And it’s part of how we prepare for the new year.
So if you spoke sharply to someone, forgot to invite someone, or didn’t follow through on a promise. You can’t just go to synagogue, say, “sorry, God,” and call it a day.
Jewish tradition says you have to go directly to that person and try to make it right.
That’s why the season leading up to Yom Kippur is just as much about repairing relationships as it is about synagogue services. Both tracks matter and they’re meant to work together.
Most people apologize the wrong way. I’m guilty of it. It is hard.
Our tradition gives us some pretty practical guidance.
Step one, be specific.
A real apology begins with saying what you actually did.
Halakha requires a, a confession of the specific wrongdoing, vidui. I’m, I can’t even with these words anymore. I hate it. Vague words like, “sorry about earlier” can leave the other person guessing. And phrases like, “sorry if I hurt you” aren’t really apologies at all. They question whether harm even happened and put the responsibility on the other person’s feelings.
Instead be specific and own what you did.
” I spoke harshly to you yesterday,” or “I didn’t follow through on what I promised.”
That’s the difference between deflecting and apologizing.
Step two, drop the excuses.
Regret, charatah, is required. Excuses undermine that. The moment you add, “but I was tired,” ” but you started it,” ” but I didn’t mean to,” you’re defending yourself not apologizing.
A real apology stands on its own.
Step three show you understand.
Halakha says we need to appease the person we’ve wronged.
It’s part of making things right.
One of the most effective ways of doing that is by showing that you understand how your actions affected them.
It’s not a formal “requirement” in halacha, but it’s one way that can lead to real reconciliation.
For example, ” I know my words embarrassed you in front of others,” or “I realize I let you down when you were counting on me.”
This goes beyond listing that mistake.
It shows the other person that you see their pain, not just your own guilt.
Step four, show how you’re going to change.
Halakha requires you to commit to not repeating the sin, kabalah le’atid.
Teshuva, the word for repentance, literally means “turning.”
An apology isn’t complete without pointing to the turn. ” Next time I’ll pause before I respond,” or “I’ll set a reminder so I don’t miss the deadline.” It signals that you’re serious about Teshuva, not just about soothing your own guilt. Notice a pattern yet?
Step five, repair the damage.
Words aren’t enough if the harm is financial or material. If you broke, borrowed, or took something, the apology isn’t complete until you’ve made restitution.
Fixing the harm gives weight to your words.
So when you put all those pieces together, the difference is huge.
Instead of, “sorry, I didn’t mean it,” which usually isn’t very effective.
We end up with, ” I spoke sharply to you yesterday. I know that hurt. I regret it and I’m sorry. I am working on pausing before I respond.”
That’s what real Teshuva sounds like. And how would you feel if you were on the other side of that apology?
However, apologizing isn’t always the right move. Judaism actually says sometimes… don’t.
First, if reaching out would cause more harm.
For example, maybe it’s an ex-partner where contact would reopen old wounds, or someone who has asked for distance.
Jewish tradition says you don’t have to force that apology. Respect their boundaries.
But you also see how that could end up being a little self-serving, right? We’ve all done that. Like, “oh, I, I shouldn’t apologize. It’ll just make things worse.” So be on the lookout for yourself doing that. Figure out if it’s really true.
Second, when the apology is really about your guilt, not their healing.
Imagine apologizing to a former coworker just so you can feel lighter, but it drags them back into pain. Teshuva isn’t about clearing your conscience, it’s about caring for the other person.
Third, when it’s performative. P ublic apologies, for instance on social media, that embarrass someone or pressure them to forgive.
Those aren’t what Yom Kippur is about. The goal isn’t to look good. It’s to make things right.
At the end of the day, the High Holiday season is about integrity, not box-checking.
A Jewish apology isn’t about the ritual of saying, “I’m sorry,” it’s about repairing what can actually be repaired.
And knowing when silence or restraint is the kinder choice.
How many times should you apologize? Judaism has a number: three.
In Jewish tradition, forgiveness isn’t about endless begging. It has a boundary. It’s a balance: humility without humiliation. Three strikes, and you’re actually free kinda.
You can’t control forgiveness, but you can control your Teshuva.
Tradition says you’re only required to ask forgiveness three times.
If you make a sincere apology three different times, and the other person still refuses to forgive, that’s their right.
The responsibility shifts to them. At that point, you’ve done your part.
But here’s the catch. It doesn’t mean you get a free pass. Even if the other person won’t forgive, you are still responsible for the other parts of Teshuva: for reflecting, turning, and changing your behavior so you don’t repeat it.
It’s a balance. You’re called to show up with humility and persistence to show you’re serious. But you’re not asked to beg forever, and you’re not defined by someone else’s refusal.
As we head into the new Jewish year, here’s my challenge for you: think of one apology you’ve been avoiding.
Yeah, that one.
Can you make it specific, sincere, and focused on change? This season is about repair: with others, with ourselves, and with Hashem.
At the time of recording this, we’ve got exactly two weeks until Rosh Hashanah. If that makes your stomach flip flop, I’m with you.
If the preparation for that already feels confusing or overwhelming, I’ve got new checklists. You know your girl, you know I love checklists.
I created The Essential Jewish Holiday Planning Guide, and it’s filled with checklists, prompts, and practical tools so you can walk into the High Holidays with more calm and less chaos.
And because I’m neurodivergent, it’s made to work with all brains.
You can grab your copy at Building a Jewish Life.com and give Future You a smoother, more meaningful season.
