Aside from fasting for 25 hours, one of the most challenging requirements of the Day of Atonement is asking forgiveness from someone we hurt or offended in the past year.

“Coming to Yom Kippur and banging on your chest doesn’t do anything. God doesn’t forgive on your behalf. It doesn’t work that way,” said Zev M. Shandalov, a former Chicago pulpit rabbi and an educator, lecturer, author, and community rabbi in Ma’aleh Adumim since 2009.

“We have to go to that person and ask for forgiveness with a heartfelt ‘I’m sorry.’ The struggle today versus, let’s say, just 20 years ago is how that apology should appear.”

Avoiding uncomfortable face-to-face confrontations is easier than ever. We can send texts or voice messages, write emails, or post on social media our requests for forgivenessmehila, in Hebrew. 

Do these modern modes of communication count, or are they just cowardly cop-outs?

Jews praying for forgiveness (selichot), at the Western Wall in the Old City of Jerusalem, on the eve of Yom Kippur, October 1, 2025
Jews praying for forgiveness (selichot), at the Western Wall in the Old City of Jerusalem, on the eve of Yom Kippur, October 1, 2025 (credit: CHAIM GOLDBERG/FLASH90)

Be authentic

Hillel Fuld, a tech columnist and Israel advocate with approximately 750,000 social-media followers, spends a lot of time interacting with people online. 

Yet when it comes to apologizing, he said, “sending a text message just doesn’t feel authentic. I get a ton of mass messages before Yom Kippur – Please forgive me, blah, blah, blah – but I don’t do that. If you’re going to ask forgiveness, be authentic about it.”

Fuld said that if he feels the need to beg someone’s pardon, “I don’t care if we’re in the digital age or not – I’m gonna get in my car and go meet that person.”

Shandalov, too, said that “the best option is to physically go to the person asking for forgiveness.” He cited the 12th-century sage Maimonides (Rambam), who wrote that proper repentance requires meeting with the wronged party.

“Of course, the Rambam didn’t have WhatsApp, but he could have said it’s okay to write a letter. But he says no, you have to have an interaction with the person and truly ask for forgiveness,” Shandalov said.

“If that’s not possible, do it in a video chat or phone call. However, sometimes saying ‘I’m sorry’ directly is a very tough thing to do. A voice note is the next best option because at least the recipient can hear the inflection in the sender’s voice.”

He considers the least desirable method to be a “general vanilla message on Facebook that says, ‘To all those whom I might have hurt, I’m sorry.’ There’s no meaning behind that.”

Nobody wants to be a checklist item

A different perspective on mass apology messages is offered by lecturer and author Oriya Mevorach, whose Afarkeset Institute provides educational tools, lectures, and workshops for navigating postmodern and Western culture through a Jewish worldview.

“The problem is not the medium,” she said.

“It’s even a blessing today that we have the opportunity to write something general. In the age of social media, we communicate with so many people – sometimes thousands of people – and we can use the same platform to make amends.”

The problem is that blanket social-media apology posts rarely include the elements necessary to trigger a forgiveness response. Instead, they may be perceived as insulting or insincere.

“What people don’t want to see is that you’re saying sorry as a checklist item. Nobody wants to be a checklist item,” she said.

“When I want someone to ask me for forgiveness, first I would like them to acknowledge what they did wrong; and second, to acknowledge that they know I was insulted or offended by what they did. If a general message would include even just the first part, it’s not that bad,” Mevorach explained.

“If a person would write, for example, ‘I know I often come across as offensive and I sometimes attack people online, and I’m aware of this weakness of mine, and I want to apologize to anyone who was insulted by me,’ I think that’s legit,” she said. “The text must be elaborated enough so people understand we are taking responsibility for a specific action.”

The ideal approach, however, is to send a direct personal message containing “the exact words that the recipient would like to hear.”

Because many of us may have difficulty crafting such a message, she suggests using AI tools such as ChatGPT to help phrase a personalized request for mehila.

Accepting a texted apology

The wording of a texted apology will determine how it is received, Shandalov agreed.

“If you feel the text message that someone sends you is adequate, then accept the apology, say ‘thank you very much,’ and put it behind you,” he counseled.

“But if you can’t accept it, you should respond, ‘Listen, I think this requires more of a discussion. I don’t want to make you feel awkward, but we need to talk about some stuff before I could really give you true forgiveness.’ And that’s fine.”

Jewish tradition stipulates that one is permitted to spurn an apology twice, “because sometimes we can’t forgive something or we don’t think the apology is sincere. By the third time you have to say, ‘Yes, I forgive you.’ If you don’t, you are considered a rasha, a bad person – although it depends on the specific situation,” he added.

According to Shandalov, one must ask for mehila even from a deceased person by vocalizing the apology at the person’s grave.

But as Fuld can attest, it’s certainly preferable to seek forgiveness while the wronged party is still among the living.

Years ago, he got into a heated political discussion with an unknown commenter on his Facebook page. “Unfortunately, I lost my cool and called him a self-hating Jew,” he recalled.

A week later, Fuld was asked by the marketing department of a client company to participate in a phone call pitching the company’s story to a journalist.

“At the end of the conversation, the journalist is like, ‘Okay, fantastic, I’ll write the story. Oh, and Hillel, by the way: Remember the guy you called a self-hating Jew last week on Facebook? That was me.’”

People are silhouetted as they pose with mobile devices in front of a screen projected with a Facebook logo, in this picture illustration taken in Zenica October 29, 2014.
People are silhouetted as they pose with mobile devices in front of a screen projected with a Facebook logo, in this picture illustration taken in Zenica October 29, 2014. (credit: REUTERS/DADO RUVIC)

Fuld felt devastated.

“When you’re on the Internet, you don’t put a face to it. Speaking to someone whom I called that name was really upsetting for me. So I apologize profusely, and he’s like, ‘It’s totally cool. I know how the Internet works. We get worked up. Totally fine, all good.’ And that was the end of that.”

A few days later, Fuld was shocked to hear that the journalist had died suddenly and unexpectedly. “I was so grateful that I’d had a chance to make it right with him. The fact that I was able to correct my mistake before he died was of astronomic importance to me.”

The Talmud, said Shandalov, encourages us to emulate God’s attributes. “God is described as mohel v’sole’ah, forgiving and pardoning. So it’s important to understand that granting forgiveness is not just repairing a relationship. It’s a godly act.”