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  • Writer's pictureEvan Wolkenstein

How To Apologize Like You Mean It

Every year, the Jewish holiday Yom Kippur comes around and gives us the opportunity to apologize to people we have harmed. For those of us who observe Yom Kippur, it forces us to think deeply about the ups and downs of interpersonal repair. For those of us who don’t celebrate Yom Kippur, it can be like being in Las Vegas during a NASCAR championship: you can enjoy the experience vicariously. Just swap out hordes of NASCAR fans and exhaust fumes for ornery, hypoglycemic Jews.

Teshuva is the main thing we Yom Kippur enthusiasts do on the 10th day of the Jewish month of Tishrei. Teshuva is usually translated as “repentance,”(though yuck – hate that word). And every year, I hear someone quote the medieval Spanish Rabbi Moshe Ben Maimon’s formula for “doing teshuva.”

Step 1: Admit how you effed up. (Mishneh Torah 1:1).Step 2: Show that you’re sorry, and take whatever actions you need to make sure you don’t eff up again. (Mishneh Torah 2:2) and fix whatever damage you’ve caused (Mishneh Torah 2:9).Step 3: Don’t eff up again if you’re ever in the same position in the future. (Mishneh Torah 2:1).

On the one hand, this is great stuff. I wish people did this more often. I should do this more often.

On the other hand, the simplicity of these steps reminds me a bit of “Dick in a Box.” Step 1, Step 2, Step 3, and “That’s the way you doooo it.”

The Dick-in-a-Box Sorry System is great for situations where the “wrong” is totally clear: for any version of stepping on someone’s foot.

“One. I’m sorry I stepped on your foot. Two. I will keep an eye out for your feet. Three. Here’s a new pair of shoes. Teshuva! That’s the way you doooo it.”

And being married, I see that daily “teshuva” is an integral part of sharing a home and a life with someone. Through teshuva, I have learned to close the cabinet doors, to clean the cat’s litter box without being asked to, and to communicate when I will be home later than I’d expected.

And if we’re lucky, that type of apologizing is good for, say, 95% of the conflicts that arise in a given year, whether at home or at work or with friends. But for that other 5%, Yom Kippur forces us to confront the fact that any real conflict – certainly one which has lingered in our minds for months – is likely to be the result of a messed up relationship system. And when the relationship is effed up, “apologizing for harm” and “promising not to do it again” strikes me as a serious oversimplification. And any approach to a complex problem with an over-simplified solution will be disappointing. Sometimes dangerous.

An example: someone has mistreated you regularly. Then they come to you and ask for forgiveness for “any time they might have harmed you.” Their Dick-in-a-Box apology doesn’t allow for you to express the fact that the relationship is unbalanced and toxic. It puts you in a situation of disempowerment, like those awkward scenes in rom-coms where the evil Alpha Male, astride a white horse, “asks” the female lead to marry him while the whole kingdom (and his armed guards) watch; she has no real agency. And Yom Kippur lurking around the corner adds that whole “kingdom watching” element. It’s not fair.

Forgiveness is not a right. And an apology is not sufficient.

The flip side, though, is also true: when apologizing to someone, never simply apologize for “anything you might have done” (gah!) and don’t just name the thing (“I’m sorry for stepping on your shoes”).

Rather: and here’s the toughest thing of all. If you want to apologize, approach someone with the desire to make things better, and ask if they’d like to speak first. Don’t see it as an opportunity to harvest an apology–see it as the chance to learn something.

We don’t live in a world of sin and repentance; rather, we live in a world of complex, competing needs with many, many unfortunate consequences as we try to meet our needs. For those of us who are celebrating Yom Kippur tomorrow night, and for those of us who are not, may we choose our approach to apologies not with a goal in mind, but with the desire to understand. With the willingness to be told the Truth.

And that’s the way you dooooo it.

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